Organoboron chemistry

<h2 id="properties-of-the-b-c-bond">Properties of the B-C bond</h2>
The C-B bond has low polarity (<a href="/facts/Electronegativity/H7Vq7Uah">electronegativity</a> 2.55 for carbon and 2.04 for boron). Alkyl boron compounds are in general stable, though easily oxidized.
Boron often forms <a href="/facts/Electron-deficient_compound/3fBwxBBH">electron-deficient compounds</a> without a full <a href="/facts/Octet_rule/X9jxSsos">octet</a>, such as the triorganoboranes. These compounds are strong <a href="/facts/Electrophile/1AHFg1zm">electrophiles</a>, but typically too sterically hindered to <a href="/facts/Dimer_(chemistry)/mU64PnEq">dimerize</a>. Electron donation from <a href="/facts/Vinyl_group/SyXSgVnw">vinyl</a> and <a href="/facts/Aryl/M3z7QRXd">aryl</a> groups can lend the C-B bond some <a href="/facts/Double_bond/qDemMn0c">double bond</a> character.

<h2 id="classes-of-organoboron-compounds">Classes of organoboron compounds</h2>
<h3>Organoboranes</h3>

The most-studied class of organoboron compounds has the formula BRnH3−n. These compounds are catalysts, reagents, and synthetic intermediates. Except a few bulky derivatives, the primary and secondary hydrides (n = 1 or 2) are, like <a href="/facts/Diborane/k7egwbPf">diborane</a> itself, strongly <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acidic</a> and dimerize in condensed phases. The trialkyl and triaryl derivatives, e.g. <a href="/facts/Triethylboron/qLlyzN2r">triethylboron</a>, are typically only weakly <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acidic</a>, and form monomers with a <a href="/facts/Trigonal_planar_molecular_geometry/935Tdp3Y">trigonal, planar</a> boron center.<a class="footnote-ref" id="fnref:4" href="#fn:4">4</a> 
Monoalkyl boranes are relatively rare. When the alkyl group is small, such as methyl, monoalkylboranes often <a href="/facts/Redistribution_reaction/pdbYLmRB">redistribute</a> to mixtures of diborane and di- and trialkylboranes. One example of an isolable (bulky) primary borane is <a href="/facts/Thexylborane/lq6pISgn">thexylborane</a> (ThxBH2), produced by the hydroboration of <a href="/facts/Tetramethylethylene/mTrWv55p">tetramethylethylene</a>:<a class="footnote-ref" id="fnref:5" href="#fn:5">5</a> A chiral example is monoisopinocampheylborane, obtained by hydroboration of (−)‐α‐pinene with <a href="/facts/Borane_dimethyl_sulfide/2TvG1KpB">borane dimethyl sulfide</a>. Although often written as IpcBH2, it is a dimer, [IpcBH2]2.<a class="footnote-ref" id="fnref:6" href="#fn:6">6</a>
Dialkylboranes are also rare with small alkyls. One common preparation reduces dialkylhalogenoboranes with metal hydrides.<a class="footnote-ref" id="fnref:7" href="#fn:7">7</a> An important application in <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a> is transmetallation to form <a href="/facts/Organozinc_compounds/xpcLJCT4">organozinc compounds</a>.<a class="footnote-ref" id="fnref:8" href="#fn:8">8</a><a class="footnote-ref" id="fnref:9" href="#fn:9">9</a> Nevertheless, some diaryl and dialkylboranes are well known. Dimesitylborane is a dimer (C6H2Me3)4B2H2) that reacts only slowly with simple terminal alkenes. It adds to alkynes to give alkenylboranes.<a class="footnote-ref" id="fnref:10" href="#fn:10">10</a> A hindered dialkylborane is <a href="/facts/Disiamylborane/1ykzzQAQ">disiamylborane</a>, abbreviated Sia2BH, also a dimer. Owing to its steric bulk, it selectively hydroborates less hindered, usually terminal alkenes in the presence of more substituted alkenes.<a class="footnote-ref" id="fnref:11" href="#fn:11">11</a> Disiamylborane must be freshly prepared as its solutions can only be stored at 0 °C for a few hours. Dicyclohexylborane Chx2BH exhibits improved thermal stability than Sia2BH. 
A versatile dialkylborane is <a href="/facts/9-BBN/8TMvv7m5">9-BBN</a>. Also called "banana borane", it exists as a dimer. It can be distilled without decomposition at 195 °C (12mm Hg). Reactions with 9-BBN typically occur at 60–80 °C, with most alkenes reacting within one hour. Tetrasubstituted alkenes add 9-BBN at elevated temperature. Hydroboration of alkenes with 9-BBN proceeds with excellent regioselectivity. It is more sensitive to steric differences than Sia2BH, perhaps because of it rigid C8 backbone. 9-BBN is more reactive towards alkenes than alkynes.<a class="footnote-ref" id="fnref:12" href="#fn:12">12</a>

<h3>Oxyacids and esters</h3>
Compounds of the type BRn(OR)3-n are called borinic esters (n = 2), <a href="/facts/Boronic_ester/BtN4s5B4">boronic esters</a> (n = 1), and <a href="/facts/Borate/5XwkBTv1">borates</a> (n = 0). Boronic acids are key to the <a href="/facts/Suzuki_reaction/aRISucCH">Suzuki reaction</a>. <a href="/facts/Trimethyl_borate/h15TFhEE">Trimethyl borate</a>, debatably not an organoboron compound, is an intermediate in sodium borohydride production.

<h3>Adducts</h3>
Boranes and borinic, boronic, and borate esters all form adducts with appropriate Lewis bases. 
Strong <a href="/facts/Base_(chemistry)/M9wA7qeM">bases</a> do not <a href="/facts/Deprotonation/SmUSh369">deprotonate</a> boranes of the form R2BH. Instead these reactions afford the octet-complete <a href="/facts/Adduct/vBpTmotm">adduct</a> R2HB-base.<a class="footnote-ref" id="fnref:13" href="#fn:13">13</a> 
<a href="/facts/N-Heterocyclic_Carbene/g4U9YPae">NHCs</a> and boranes form stable NHC-borane adducts.<a class="footnote-ref" id="fnref:14" href="#fn:14">14</a> <a href="/facts/Triethylborane/qLlyzN2r">Triethylborane</a> adducts can be synthesised directly from the <a href="/facts/Imidazolium_salt/5MybM6Hh">imidazolium salt</a> and <a href="/facts/Lithium_triethylborohydride/6kWKrvwn">lithium triethylborohydride</a>. 

<h3>Polyhedral clusters</h3>
Boron is <a href="/facts/Borohydride_cluster/wu3RTzUS">renowned for cluster species</a>, e.g. <a href="/facts/Dodecaborate/a38Vf0nE">dodecaborate</a> [B12H12]2-. Such clusters have many organic derivatives. One example is [B12(CH3)12]2- and its radical derivative [B12(CH3)12]−.<a class="footnote-ref" id="fnref:15" href="#fn:15">15</a> Related <a href="/facts/Cluster_chemistry/EsuLgxJU">cluster compounds</a> with carbon vertices are <a href="/facts/Carborane/rBGVnA2R">carboranes</a>; the best known is orthocarborane, C2B10H12. Carboranes have few commercial applications. Anionic derivatives such as [C2B9H11]2−, called dicarbollides, <a href="/facts/Ligand/6etB3qeW">ligate</a> similarly to <a href="/facts/Cyclopentadienide/11slGTQo">cyclopentadienide</a>.
Borane cluster structures are built from the <a href="/facts/Triboracyclopropenyl/5xDo2SIB">triangular (BR)3 unit</a>, which is almost unknown in isolation. However, the corresponding aromatic dianion, (BR)2−3, forms from careful dehalogenation of a RNBCl2 species.<a class="footnote-ref" id="fnref:16" href="#fn:16">16</a>

<h3>Boryl complexes and radicals</h3>
Main articles: <a href="/facts/Borylation/PUMxIC17">borylation</a> and <a href="/facts/Boryl_radicals/NkfwVKD0">Boryl radicals</a>
<a href="/facts/Organometallic_compounds/bhqFz2P0">Organometallic compounds</a> with metal-boron bonds (M–BR2) are boryl complexes, corresponding to the notional boryl anion R2B−, although the latter cannot be produced through deprotonation (see § Adducts). In one synthesis, the boryl anion moiety arose through <a href="/facts/Lithium-halogen_exchange/g0zvPIU0">lithium-halogen exchange</a>: As shown, the product is <a href="/facts/Isoelectronic/SbzuaI05">isoelectronic</a> to an <a href="/facts/Persistent_carbene/g4U9YPae">N-heterocyclic carbene</a>.<a class="footnote-ref" id="fnref:17" href="#fn:17">17</a><a class="footnote-ref" id="fnref:18" href="#fn:18">18</a> 
Related ligands are <a href="/facts/Borylene/leMdbfPK">borylenes</a> (M–B(R)–M).

<h3>Unsaturated compounds</h3>
Alkylideneboranes (RB=CRR) with a boron–carbon <a href="/facts/Double_bond/qDemMn0c">double bond</a> are rare. One example, HB=CH2, can be detected at low temperature. The derivative CH3B=C(SiMe3)2 is fairly stable, but prone to cyclodimerisation.<a class="footnote-ref" id="fnref:19" href="#fn:19">19</a>

Some boron-substituted <a href="/facts/Heterocycle/8oYSjJxY">heterocycles</a> are <a href="/facts/Aromatic_(chemistry)/wK0DzRY6">aromatic</a>, but very few such arenes are stable. In <a href="/facts/Borabenzene/nwaWYLXa">borabenzene</a>, boron replaces one CH center in benzene. Borabenzene and derivatives invariably appear as adducts, e.g., C5H5B-pyridine. The cyclic compound <a href="/facts/Borole/doJc8elx">borole</a>, a <a href="/facts/Structural_analog/3aysWSVG">structural analog</a> of <a href="/facts/Pyrrole/7c7AbyN8">pyrrole</a>, has not been isolated, but substituted derivatives (boroles) are known. The cyclic compound <a href="/facts/Borepin/8oYSjJxY">borepin</a> has been isolated and is aromatic.
Boron-boron <a href="/facts/Double_bond/qDemMn0c">multiple bonds</a> are rare, although doubly-bonded dianions have been known since the 1990s.<a class="footnote-ref" id="fnref:20" href="#fn:20">20</a> Neutral analogues use NHC adducts, such as the following <a href="/facts/Diborane(2)/8FW3ntpT">diborane(2)</a> derivative:<a class="footnote-ref" id="fnref:21" href="#fn:21">21</a><a class="footnote-ref" id="fnref:22" href="#fn:22">22</a>

Each boron atom has an attached proton and is coordinated to a <a href="/facts/NHC_carbene/g4U9YPae">NHC carbene</a>.<a class="footnote-ref" id="fnref:23" href="#fn:23">23</a><a class="footnote-ref" id="fnref:24" href="#fn:24">24</a>
A reported <a href="/facts/Diboryne/EtkulPtk">diboryne</a> is based on similar chemistry.<a class="footnote-ref" id="fnref:25" href="#fn:25">25</a>
A compound with the B≡C triple bond was synthesized for the first time in 2025.<a class="footnote-ref" id="fnref:26" href="#fn:26">26</a>

<h2 id="synthesis">Synthesis</h2>
<h3>From Grignard reagents</h3>
Simple organoboranes such as <a href="/facts/Triethylborane/qLlyzN2r">triethylborane</a> or <a href="/facts/Tris(pentafluorophenyl)boron/DpzRgHAH">tris(pentafluorophenyl)boron</a> can be prepared from <a href="/facts/Trifluoroborane/2qa0NIH8">trifluoroborane</a> (in <a href="/facts/Ether/jwDg0IKr">ether</a>) and the ethyl or pentafluorophenyl <a href="/facts/Grignard_reagent/0vkLtPo1">Grignard reagent</a>. Further <a href="/facts/Carbanion/AyYH2udQ">carbanion</a> addition will effect a borate (R4B−).
<a href="/facts/Boronic_acid/BtN4s5B4">Boronic acids</a> RB(OH)2 react with <a href="/facts/Potassium_bifluoride/MVGNmlMg">potassium bifluoride</a> K[HF2] to form <a href="/facts/Organotrifluoroborate/LxzAn7PF">trifluoroborate salts</a> K[RBF3],<a class="footnote-ref" id="fnref:27" href="#fn:27">27</a> precursors to nucleophilic alkyl and aryl boron difluorides, ArBF2:<a class="footnote-ref" id="fnref:28" href="#fn:28">28</a>

<h3>From alkenes</h3>
In <a href="/facts/Hydroboration/Wm7v7Inr">hydroboration</a>, <a href="/facts/Alkene/RtYcS6kU">alkenes</a> insert into borane B-H bonds, with <a href="/facts/Anti-Markovnikov_addition/WJokRx6l">anti-Markovnikov</a> stereochemistry. Hydroboration occurs <a href="/facts/Stereospecificity/BT4em18V">stereospecifically</a> syn — on the same alkene face. The <a href="/facts/Transition_state/34PsdqRd">transition state</a> for this <a href="/facts/Concerted_reaction/sPAIkRGa">concerted reaction</a> can be visualized as a square with the corners occupied by carbon, carbon, hydrogen and boron, maximizing overlap between the <a href="/facts/Olefin/RtYcS6kU">olefin</a> <a href="/facts/P-orbital/tKhgl6mL">p-orbitals</a> and the empty boron orbital.
Hydroboration with borane (BH3) equivalents converts only 33% of the starting olefin to product — boron-containing <a href="/facts/Byproduct/qDosnqoD">byproducts</a> consume the remainder. The <a href="/facts/Chelate_effect/4G79sXBB">chelate effect</a> improves that ratio for cyclic boron-containing reagents. One common cyclic organoboron reagent is <a href="/facts/9-Borabicyclo(3.3.1)nonane/8TMvv7m5">9-BBN</a>.<a class="footnote-ref" id="fnref:29" href="#fn:29">29</a><a class="footnote-ref" id="fnref:30" href="#fn:30">30</a>

<h3>By borylation</h3>
Main article: <a href="/facts/Borylation/PUMxIC17">Borylation</a>
Metal-catalyzed <a href="/facts/Borylation/PUMxIC17">borylation</a> reactions produce an organoboron compound from aliphatic or aromatic C-H <a href="/facts/Sigma_bond/CSyEe5CY">sigma bonds</a> via a transition-metal catalyst. A common reagent is <a href="/facts/Bis(pinacolato)diboron/Y3GrPUlJ">bis(pinacolato)diboron</a>.

<h3>From other boron compounds</h3>
<a href="/facts/Carbon_monoxide/CKuLtEMJ">Carbon monoxide</a> reacts with alkylboranes to form an unstable <a href="/facts/Borane_carbonyl/dXkRtbhh">borane carbonyl</a>. Then an alkyl substituent <a href="/facts/1%2c2-rearrangement/PubHVwnX">migrates</a> from boron to the carbonyl carbon. For example, homologated primary alcohols result from organoboranes, carbon monoxide, and a reducing agent (here, <a href="/facts/Sodium_borohydride/D2Hwts5x">sodium borohydride</a>):<a class="footnote-ref" id="fnref:31" href="#fn:31">31</a>

<h4>Alkenylboranes</h4>
Alkynylboranes attack electrophiles to give trans alkenylboranes,<a class="footnote-ref" id="fnref:32" href="#fn:32">32</a> as in the first step of this olefin synthesis:

<h2 id="reactions">Reactions</h2>

The key property of organoboranes (R3B) and borates (R4B−, generated via addition of R− to R3B) is their susceptibility to reorganization. These compounds possess boron–carbon bonds polarized toward carbon. The boron-attached carbon is nucleophilic;<a class="footnote-ref" id="fnref:33" href="#fn:33">33</a> in borates, the nucleophicity suffices for intermolecular transfer to an electrophile.<a class="footnote-ref" id="fnref:34" href="#fn:34">34</a><a class="footnote-ref" id="fnref:35" href="#fn:35">35</a>
Boranes alone are generally not nucleophilic enough to transfer an R group intermolecularly. Instead, the group <a href="/facts/1%2c2-migration/PubHVwnX">1,2-migrates</a> to an electrophilic carbon attached to boron, especially if that carbon is unsaturated or bears a good leaving group:<a class="footnote-ref" id="fnref:36" href="#fn:36">36</a>

An organic group's migration propensity depends on its ability to stabilize negative charge: alkynyl > aryl ≈ alkenyl > primary alkyl > secondary alkyl > tertiary alkyl.<a class="footnote-ref" id="fnref:37" href="#fn:37">37</a> Bis(norbornyl)borane and 9-BBN are often hydroboration reagents for this reason — only the hydroborated olefin is likely to migrate upon nucleophilic activation.
Migration retains configuration at the migrant carbon<a class="footnote-ref" id="fnref:38" href="#fn:38">38</a> and inverts it at the (presumably <a href="/facts/Orbital_hybridisation/Fl7sz8Jm">sp3-hybridized</a>) terminus.<a class="footnote-ref" id="fnref:39" href="#fn:39">39</a> The resulting reorganized borane can then be oxidized or protolyzed to a final product.

<h3>Protonolysis</h3>
Organoboranes are unstable to <a href="/facts/Br%25C3%25B8nsted%25E2%2580%2593Lowry_acid%25E2%2580%2593base_theory/bqxQnJoX">Brønsted–Lowry acids</a>, deboronating in favor of a proton. Consequently, organoboranes are easily removed from an alkane or alkene substrate, as in the second step of this olefin synthesis:<a class="footnote-ref" id="fnref:40" href="#fn:40">40</a>

<h3>Addition to halocarbonyls</h3>
α-Halo enolates are common nucleophiles in borane reorganization. After nucleophilic attack at boron, the resulting ketoboronate eliminates the halogen and tautomerizes to a neutral enolborane. A functionalized carbonyl compound then results from protonolysis,<a class="footnote-ref" id="fnref:41" href="#fn:41">41</a> or quenching with other electrophiles:

Because the migration is stereospecific, this method synthesizes enantiopure α-alkyl or -aryl ketones.<a class="footnote-ref" id="fnref:42" href="#fn:42">42</a>
α-Haloester enolates add similarly to boranes, but with lower yields:<a class="footnote-ref" id="fnref:43" href="#fn:43">43</a>

Diazoesters and diazoketones remove the requirement for external base.<a class="footnote-ref" id="fnref:44" href="#fn:44">44</a> α,α'-Dihalo enolates react with boranes to form α-halo carbonyl compounds that can be further functionalized at the α position.<a class="footnote-ref" id="fnref:45" href="#fn:45">45</a>

<h3>Addition to carbonyl functional groups</h3>
In allylboration, an <a href="/facts/Allyl_group/CDxPwyvF">allylborane</a> adds across an <a href="/facts/Aldehyde/xSIRkW03">aldehyde</a> or <a href="/facts/Ketone/BqQXpLo4">ketone</a> with an <a href="/facts/Allylic_shift/T9xfF9rV">allylic shift</a>, and can then be converted to a <a href="/facts/Homoallylic/CDxPwyvF">homoallylic</a> <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohol</a> during <a href="/facts/Workup_(chemistry)/LURlLf4C">workup</a>. The reaction is much slower with ketones than aldehydes.<a class="footnote-ref" id="fnref:46" href="#fn:46">46</a> For example, in Nicolaou's <a href="/facts/Epothilone/xLKGJy9D">epothilones</a> synthesis, asymmetric allylboration (with an allylborane derived from chiral <a href="/facts/Alpha-pinene/l9Epte63">alpha-pinene</a>) is the first step in a two-carbon <a href="/facts/Homologation_reaction/r7X7yYDt">homologation</a> to <a href="/facts/Acetogenin/Cz7QrztK">acetogenin</a>:<a class="footnote-ref" id="fnref:47" href="#fn:47">47</a>

Trifluoroborate salts are stabler than boronic acids and selectively alkylate <a href="/facts/Aldehyde/xSIRkW03">aldehydes</a>:<a class="footnote-ref" id="fnref:48" href="#fn:48">48</a>

<h3>Oxygenation</h3>
The <a href="/facts/Hydroboration-oxidation_reaction/hs7YsVtb">hydroboration-oxidation reaction pair</a> oxidizes the borane to an <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohol</a> with <a href="/facts/Hydrogen_peroxide/vju6HBIc">hydrogen peroxide</a> or to a <a href="/facts/Carbonyl/KJ71bo3X">carbonyl</a> group with <a href="/facts/Chromium_oxide/HaxtA3q8">chromium oxide</a>.
Oxidation of an alkenylborane gives an boron-free enol.<a class="footnote-ref" id="fnref:49" href="#fn:49">49</a>

<h3>Halogenation</h3>
Organoborane activation with hydroxide or alkoxide and treatment with X2 yields haloalkanes. With excess base, two of the three alkyl groups attached to the boron atom may convert to halide, but <a href="/facts/Disiamylborane/1ykzzQAQ">disiamylborane</a> permits only halogenation of the hydroborated olefin:<a class="footnote-ref" id="fnref:50" href="#fn:50">50</a>
Treatment of an alkenylborane with iodine or bromine induces migration of a boron-attached organic group. Alkynyl groups migrate selectively, forming enynes after treatment with sodium acetate and hydrogen peroxide:<a class="footnote-ref" id="fnref:51" href="#fn:51">51</a>

<h3>Transmetalation and coupling</h3>
Organoboron compounds also <a href="/facts/Transmetalation/Mm0hQzp3">transmetalate</a> easily, especially to <a href="/facts/Organopalladium/19HtzTI1">organopalladium</a> compounds. In the <a href="/facts/Suzuki_reaction/aRISucCH">Suzuki reaction</a>, an <a href="/facts/Aryl/M3z7QRXd">aryl</a>- or <a href="/facts/Vinyl_group/SyXSgVnw">vinyl</a>-<a href="/facts/Boronic_acid/BtN4s5B4">boronic acid</a> couples to an <a href="/facts/Aryl/M3z7QRXd">aryl</a>- or <a href="/facts/Vinyl_group/SyXSgVnw">vinyl</a>-<a href="/facts/Halide/ujYu8kGD">halide</a> through a <a href="/facts/Palladium/AXMwDFxs">palladium(0) complex</a> catalyst:<a class="footnote-ref" id="fnref:52" href="#fn:52">52</a>
 
 
 
 
 
 R
 
 1
 
 
 
 
 
 
 −
 
 
 BY
 
 2

+
          
            R
            
              2
            
            
              
            
          
          
            −
          
          X
          
            
              →
              
                
                  Base

Pd
                      catalyst
                    
                  
                
              
            
          
          
            R
            
              1
            
            
              
            
          
          
            −
          
          
            R
            
              2
            
            
              
            
          
        
      
    
    {\displaystyle {\ce {R1-BY2{}+R2-X->[{} \atop {\underset {\text{catalyst}}{\ce {Pd}}}][{\text{Base}}]R1-R2}}}

<h3>Reducing agents</h3>
Borane hydrides such as <a href="/facts/9-BBN/8TMvv7m5">9-BBN</a> and <a href="/facts/L-selectride/46ta6byc">L-selectride</a> (lithium tri(<a href="/facts/Sec-Butyl/fbTF0UkI">sec-butyl</a>)borohydride) are <a href="/facts/Reducing_agent/CtfSGVXC">reducing agents</a>. An <a href="/facts/Asymmetric_catalyst/5hJe37TL">asymmetric catalyst</a> for <a href="/facts/Carbonyl/KJ71bo3X">carbonyl</a> reductions is the <a href="/facts/CBS_catalyst/ku4F5Kbd">CBS catalyst</a>, which relies on boron coordination to the carbonyl oxygen.

<h2 id="other-synthetic-applications">Other synthetic applications</h2>
<h3>Alcohols</h3>
Homologated primary alcohols result from the treatment of organoboranes with carbon monoxide and a hydride:<a class="footnote-ref" id="fnref:53" href="#fn:53">53</a>

Tertiary alcohols with two identical groups attached to the alcohol carbon may be synthesized through an alkynylborane double migration:<a class="footnote-ref" id="fnref:54" href="#fn:54">54</a>

<h3>Carbonyl groups</h3>
Organoborates anions <a href="/facts/Reductive_elimination/H2SXpH0n">reductively eliminate</a> against acyl halides. Here, the borate was generated from tri(cyclopentyl)borane and phenyllithium; the three cyclopentyl groups do not significantly migrate:<a class="footnote-ref" id="fnref:55" href="#fn:55">55</a>

<h2 id="applications">Applications</h2>
Organoboron chemistry is mainly of commercial value in the pharmaceutical industry.
<a href="/facts/Triethylborane/qLlyzN2r">Triethylborane</a> was used to ignite the JP-7 fuel of the <a href="/facts/Pratt_%2526_Whitney_J58/IoKE0jWT">Pratt & Whitney J58</a> <a href="/facts/Variable_cycle_engine/juAc3RsD">variable cycle engines</a> powering the <a href="/facts/Lockheed_SR-71_Blackbird/ESfv9oFq">Lockheed SR-71 Blackbird</a>.
Organoboron compounds have long been discussed for use as <a href="/facts/Boron_neutron_capture_therapeutics/mqkau0u0">boron delivery agents</a> in <a href="/facts/Neutron_capture_therapy_of_cancer/FDbdUNkY">neutron capture therapy of cancer</a>.<a class="footnote-ref" id="fnref:56" href="#fn:56">56</a>

<h3>Further reading</h3>
<ul><li>Thomas, Susan E. The Roles of Boron and Silicon. Oxford Chemistry Primers No. 1; 1991.</li></ul>
<h3>Footnotes</h3>

<h2 id="references">References</h2>

<ol>
<li id="fn:1">Thomas 1991 - Thomas, Susan E. The Roles of Boron and Silicon. Oxford Chemistry Primers No. 1; 1991. <a href="#fnref:1" class="footnote-back-ref">↩</a></li>
<li id="fn:2">Elschenbroich, Christoph. Organometallics 3rd Ed. 2006 ISBN 3-527-29390-6 – Wiley-VCH, Weinheim <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></li>
<li id="fn:3">Negishi E.-I.; Idacavage, M. J. Org. React. 1985, 33, 1. doi:10.1002/0471264180.or033.01 <a href="/wiki/Org._React." target="_blank">/wiki/Org._React.</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></li>
<li id="fn:4">Brown, H. C. Organic Syntheses via Boranes John Wiley & Sons, Inc. New York: 1975. ISBN 0-471-11280-1. <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></li>
<li id="fn:5">Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis. 1974 (2): 77–89. doi:10.1055/s-1974-23248. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></li>
<li id="fn:6">Dhar, Raj K.; Josyula, Kanth V. B.; Todd, Robert; Gagare, Pravin D.; Ramachandran, Veeraraghavan (2001). "Diisopinocampheylborane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–10. doi:10.1002/047084289X.rd248.pub3. ISBN 9780470842898. <a href="9780470842898" target="_blank">9780470842898</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></li>
<li id="fn:7">Brown, H. C.; Kulkarni, S. U. (1981). "Organoboranes: XXV. Hydridation of dialkylhaloboranes. New practical syntheses of dialkylboranes under mild conditions". Journal of Organometallic Chemistry. 218: 299. doi:10.1016/S0022-328X(00)81001-3. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></li>
<li id="fn:8">Boudier, A.; Hupe, E.; Knochel, P. (2000). "Highly Diastereoselective Synthesis of Monocyclic and Bicyclic Secondary Diorganozinc Reagents with Defined Configuration". Angewandte Chemie International Edition. 39 (13): 2294–2297. doi:10.1002/1521-3773(20000703)39:13<2294::AID-ANIE2294>3.0.CO;2-J. PMID 10941068. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></li>
<li id="fn:9">Hupe, E.; Knochel, P. (2001). "Stereoselective Synthesis of Secondary Organozinc Reagents and Their Reaction with Heteroatomic Electrophiles". Organic Letters. 3 (1): 127–30. doi:10.1021/ol0068400. PMID 11429854. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></li>
<li id="fn:10">Pelter, A.; Singaram, S.; Brown, H. C. (1983). "The Dimesitylboron Group in Organic Chemistry. 6 Hydroborations with dimesitylborane". Tetrahedron Letters. 24 (13): 1433. doi:10.1016/S0040-4039(00)81675-5. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></li>
<li id="fn:11">Dodd, D.S.; Ochlschlager, A. C. (1992). "Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone". Journal of Organic Chemistry. 57 (10): 2794. doi:10.1021/jo00036a008. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></li>
<li id="fn:12">Dhillon, R. S. (2007). Hydroboration and Organic Synthesis : 9-Borabicyclo [3.3.1] Nonane (9-BBN). Springer. <a href="#fnref:12" class="footnote-back-ref">↩</a></li>
<li id="fn:13">Hall, Dennis G. Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine. ISBN 3-527-30991-8 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></li>
<li id="fn:14">Curran, D. P.; Solovyev, A.; Makhlouf, Brahmi M.; Fensterbank, L.; Malacria, M.; Lacôte, E. (2011). "Synthesis and Reactions of N-Heterocyclic Carbene Boranes". Angewandte Chemie International Edition. 50 (44): 10294–10317. doi:10.1002/anie.201102717. PMID 21898724. <a href="/wiki/Louis_Fensterbank" target="_blank">/wiki/Louis_Fensterbank</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></li>
<li id="fn:15">Grimes, R. N. (2016). Carboranes (3rd ed.). New York: Academic Press. ISBN 9780128019054. <a href="9780128019054" target="_blank">9780128019054</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></li>
<li id="fn:16">Kupfer, Thomas; Braunschweig, Holger; Radacki, Krzysztof (2015-12-07). "The Triboracyclopropenyl Dianion: The Lightest Possible Main-Group-Element Hückel π Aromatic". Angewandte Chemie International Edition. 54 (50): 15084–15088. doi:10.1002/anie.201508670. PMID 26530854. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></li>
<li id="fn:17">Segawa Yasutomo; Yamashita Makoto; Nozaki Kyoko (2006). "Boryllithium: Isolation, Characterization, and Reactivity as a Boryl Anion". Science. 314 (5796): 113–115. Bibcode:2006Sci...314..113S. doi:10.1126/science.1131914. PMID 17023656. S2CID 21040230. <a href="/wiki/Science_(journal)" target="_blank">/wiki/Science_(journal)</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></li>
<li id="fn:18">Halford, Bethany. "Attacks: Electropositive element pressed into action as nucleophilic boryllithium" Chemical & Engineering News 2006; Volume 84 (41): 11
 <a href="http://pubs.acs.org/cen/news/84/i41/8441notw8.htmlBoron" target="_blank">http://pubs.acs.org/cen/news/84/i41/8441notw8.htmlBoron</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></li>
<li id="fn:19">Paetzold, Peter; Englert, Ulli; Finger, Rudolf; Schmitz, Thomas; Tapper, Alexander; Ziembinski, Ralf (2004). "Reactions at the Boron-Carbon Double Bond of Methyl(methylidene)boranes". Z. Anorg. Allg. Chem. 630 (4): 508–518. doi:10.1002/zaac.200300396. <a href="https://doi.org/10.1002%2Fzaac.200300396" target="_blank">https://doi.org/10.1002%2Fzaac.200300396</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></li>
<li id="fn:20">Power, Philip P. (2003) [19 July 2002]. "Persistent and stable radicals of the heavier main group elements and related species". Chemical Reviews. 103. American Chemical Society: 792. doi:10.1021/cr020406p. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></li>
<li id="fn:21">Wang Yuzhong; Quillian, Brandon; Wei Pingrong; Chaitanya, S. Wannere; Xie Yaoming; King, R. Bruce; Schaefer III, Henry F.; v. R. Schleyer, Paul; Robinson, Gregory H. (2007). "A Stable Neutral Diborene Containing a B=B Double Bond". J. Am. Chem. Soc. 129 (41): 12412–12413. doi:10.1021/ja075932i. PMID 17887683. <a href="/wiki/R._Bruce_King" target="_blank">/wiki/R._Bruce_King</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></li>
<li id="fn:22">Dagani, Ron. "Neutral Diborene Is A First" Chemical & Engineering News October 1, 2007 Volume 85, Number 40 p. 10 <a href="http://pubs.acs.org/cen/news/85/i40/8540notw7.html" target="_blank">http://pubs.acs.org/cen/news/85/i40/8540notw7.html</a> <a href="#fnref:22" class="footnote-back-ref">↩</a></li>
<li id="fn:23">Braunschweig, Holger; Dewhurst, Rian D. (2013-03-25). "Single, Double, Triple Bonds and Chains: The Formation of Electron-Precise B-B Bonds". Angewandte Chemie International Edition. 52 (13): 3574–3583. doi:10.1002/anie.201208189. ISSN 1521-3773. PMID 23362015. <a href="/wiki/Holger_Braunschweig" target="_blank">/wiki/Holger_Braunschweig</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></li>
<li id="fn:24">Arrowsmith, Merle; Braunschweig, Holger; Stennett, Tom E. (2017-01-02). "Formation and Reactivity of Electron-Precise B−B Single and Multiple Bonds" (PDF). Angewandte Chemie International Edition. 56 (1): 96–115. doi:10.1002/anie.201610072. ISSN 1521-3773. PMID 27860056. Archived (PDF) from the original on July 22, 2018. <a href="https://opus.bibliothek.uni-wuerzburg.de/opus4-wuerzburg/frontdoor/deliver/index/docId/14563/file/Braunschweig_Preprint_Electron-Precise_B-B_Single_Multiple_Bonds_2016.pdf" target="_blank">https://opus.bibliothek.uni-wuerzburg.de/opus4-wuerzburg/frontdoor/deliver/index/docId/14563/file/Braunschweig_Preprint_Electron-Precise_B-B_Single_Multiple_Bonds_2016.pdf</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></li>
<li id="fn:25">Braunschweig, Holger; Dewhurst, Rian D.; Hammond, Kai; Mies, Jan; Radacki, Krzysztof; Vargas, Alfredo (15 June 2012). "Ambient-temperature isolation of a compound with a boron-boron triple bond". Science. 336 (6087): 1420–1422. doi:10.1126/science.1221138. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:25" class="footnote-back-ref">↩</a></li>
<li id="fn:26">Michel, Maximilian; Kar, Sourav; Endres, Lukas; Dewhurst, Rian D.; Engels, Bernd; Braunschweig, Holger (2025-03-04). "The synthesis of a neutral boryne". Nature Synthesis: 1–8. doi:10.1038/s44160-025-00763-1. ISSN 2731-0582. <a href="https://www.nature.com/articles/s44160-025-00763-1" target="_blank">https://www.nature.com/articles/s44160-025-00763-1</a> <a href="#fnref:26" class="footnote-back-ref">↩</a></li>
<li id="fn:27">Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. (1995). "Conversion of Arylboronic Acids into Potassium Aryltrifluoroborates: Convenient Precursors of Arylboron Difluoride Lewis Acids". J. Org. Chem. 60 (10): 3020–3027. doi:10.1021/jo00115a016. <a href="/wiki/J._Org._Chem." target="_blank">/wiki/J._Org._Chem.</a> <a href="#fnref:27" class="footnote-back-ref">↩</a></li>
<li id="fn:28">Molander, Gary A.; Canturk, Belgin (2009). "Organotrifluoroborates and Monocoordinated Palladium Complexes as Catalysts—A Perfect Combination for Suzuki–Miyaura Coupling". Angew. Chem. Int. Ed. 48 (49): 9240–9261. doi:10.1002/anie.200904306. PMC 2917751. PMID 19899086. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2917751" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2917751</a> <a href="#fnref:28" class="footnote-back-ref">↩</a></li>
<li id="fn:29">Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry. ISBN 0-306-41088-5 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:29" class="footnote-back-ref">↩</a></li>
<li id="fn:30">Jacob III, P.; Brown, H. C. J. Org. Chem. 1977, 42, 579. <a href="#fnref:30" class="footnote-back-ref">↩</a></li>
<li id="fn:31">Rathke, M. W.; Brown, H. C. J. Am. Chem. Soc. 1967, 89, 2740. <a href="#fnref:31" class="footnote-back-ref">↩</a></li>
<li id="fn:32">Corey, E. J.; Ravindranathan, T. J. Am. Chem. Soc. 1972, 94, 4013. <a href="#fnref:32" class="footnote-back-ref">↩</a></li>
<li id="fn:33">Allred, A. L.; Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 5, 264. <a href="#fnref:33" class="footnote-back-ref">↩</a></li>
<li id="fn:34">Negishi E.-I. J. Organometal. Chem. 1976, 108, 281. <a href="#fnref:34" class="footnote-back-ref">↩</a></li>
<li id="fn:35">Negishi E.-I.; Idacavage, M. J. Org. React. 1985, 33, 1. doi:10.1002/0471264180.or033.01 <a href="/wiki/Org._React." target="_blank">/wiki/Org._React.</a> <a href="#fnref:35" class="footnote-back-ref">↩</a></li>
<li id="fn:36">Negishi E.-I. J. Organometal. Chem. 1976, 108, 281. <a href="#fnref:36" class="footnote-back-ref">↩</a></li>
<li id="fn:37">Miyaura M.; Sasaki N.; Itoh M.; Suzuki A. Tetrahedron Lett. 1977, 173. <a href="#fnref:37" class="footnote-back-ref">↩</a></li>
<li id="fn:38">Zweifel, G. in Aspects of Mechanism and Organometallic Chemistry, J. H. Bewster, Ed., Plenum, 1978, p. 229. <a href="#fnref:38" class="footnote-back-ref">↩</a></li>
<li id="fn:39">Midland, M. M.; Zolopa, A. R.; Halterman, R. L. J. Am. Chem. Soc. 1979, 101, 248. <a href="#fnref:39" class="footnote-back-ref">↩</a></li>
<li id="fn:40">Corey, E. J.; Ravindranathan, T. J. Am. Chem. Soc. 1972, 94, 4013. <a href="#fnref:40" class="footnote-back-ref">↩</a></li>
<li id="fn:41">Brown, H. C.; Rogic M. M.; Nambu H.; Rathke, M. W. J. Am. Chem. Soc. 1969, 91, 2147. <a href="#fnref:41" class="footnote-back-ref">↩</a></li>
<li id="fn:42">Nesmeyanov, A. N.; Sokolik, R. A. The Organic Compounds of Boron, Aluminium, Gallium, Indium, and Thallium, North-Holland, Amsterdam, 1967. <a href="#fnref:42" class="footnote-back-ref">↩</a></li>
<li id="fn:43">Brown, H. C.; Rogic, M. M.; Rathke, M. W.; Kabalka, G. W. J. Am. Chem. Soc. 1968, 90, 818. <a href="#fnref:43" class="footnote-back-ref">↩</a></li>
<li id="fn:44">Hooz, J.; Gunn, D. M. J. Am. Chem. Soc. 1969, 91, 6195. <a href="#fnref:44" class="footnote-back-ref">↩</a></li>
<li id="fn:45">Pasto, D. J.; Wojtkowski, P. W. J. Org. Chem. 1971, 36, 1790. <a href="#fnref:45" class="footnote-back-ref">↩</a></li>
<li id="fn:46">Lachance, H.; Hall, D. (2008). "Allylboration of Carbonyl Compounds". Organic Reactions. Vol. 73. p. 1. doi:10.1002/0471264180.or073.01. ISBN 978-0471264187. <a href="978-0471264187" target="_blank">978-0471264187</a> <a href="#fnref:46" class="footnote-back-ref">↩</a></li>
<li id="fn:47">Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Finlay, M. R. V.; Boddy, C. N. C. (1998). "Probing the Ring Size of Epothilones: Total Synthesis of 14-, 15-, 17-, and 18 Epothilones A". Angewandte Chemie International Edition in English. 37 (1–2): 81–84. doi:10.1002/(sici)1521-3773(19980202)37:1/2<81::aid-anie81>3.0.co;2-c. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:47" class="footnote-back-ref">↩</a></li>
<li id="fn:48">Batey, Robert A.; Quach Tan D.; Shen Ming; Thadani, Avinash N.; Smil, David V.; Li Sze-Wan; MacKay, D. Bruce (2002). "Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed C–C bond-forming reactions" (PDF). Pure Appl. Chem. 74 (1): 43–55. doi:10.1351/pac200274010043. S2CID 49223984. <a href="http://www.iupac.org/publications/pac/2002/pdf/7401x0043.pdf" target="_blank">http://www.iupac.org/publications/pac/2002/pdf/7401x0043.pdf</a> <a href="#fnref:48" class="footnote-back-ref">↩</a></li>
<li id="fn:49">Midland, M. M.; Brown, H. C. J. Org. Chem. 1975, 40, 2845. <a href="#fnref:49" class="footnote-back-ref">↩</a></li>
<li id="fn:50">Brown, H. C.; Rathke, M. W.; Rogic, M. M. J. Am. Chem. Soc. 1968, 90, 5038. <a href="#fnref:50" class="footnote-back-ref">↩</a></li>
<li id="fn:51">Negishi, E.-i.; Lew, G.; Yoshida T. Chem. Commun. 1973, 874. <a href="#fnref:51" class="footnote-back-ref">↩</a></li>
<li id="fn:52">Miyaura Norio; Suzuki Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007. S2CID 53050782. <a href="/wiki/Norio_Miyaura" target="_blank">/wiki/Norio_Miyaura</a> <a href="#fnref:52" class="footnote-back-ref">↩</a></li>
<li id="fn:53">Rathke, M. W.; Brown, H. C. J. Am. Chem. Soc. 1967, 89, 2740. <a href="#fnref:53" class="footnote-back-ref">↩</a></li>
<li id="fn:54">Midland, M. M.; Brown, H. C. J. Org. Chem. 1975, 40, 2845. <a href="#fnref:54" class="footnote-back-ref">↩</a></li>
<li id="fn:55">Negishi E.-I.; Abramovitch, A.; Merrill, R. E. Chem. Commun. 1975, 138. <a href="#fnref:55" class="footnote-back-ref">↩</a></li>
<li id="fn:56">Barth, Rolf F.; Mi, Peng; Yang, Weilian (December 2018). "Boron delivery agents for neutron capture therapy of cancer". Cancer Communications. 38 (1): 35. doi:10.1186/s40880-018-0299-7. ISSN 2523-3548. PMC 6006782. PMID 29914561. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6006782" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6006782</a> <a href="#fnref:56" class="footnote-back-ref">↩</a></li>
</ol>

Organoboron chemistry open-in-new

Organoboron chemistry