Organotrifluoroborate

<h2 id="structure">Structure</h2>
<table><tbody><tr><td></td><td></td></tr><tr><td><a href="/facts/Thermal_ellipsoid/rs75Fjvz">thermal ellipsoid</a> model of [PhBF3]−, as foundin the <a href="/facts/Crystal_structure/bJ4bCeHd">crystal structure</a> of K[PhBF3]<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a></td><td><a href="/facts/Space-filling_model/PcHWmvfV">space-filling</a> packing diagram ofthe crystal structure of K[PhBF3]<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></td></tr></tbody></table>
<h2 id="synthesis">Synthesis</h2>
<p class="note">See also: <a href="/facts/Organoboron_chemistry/r6NQHXYt">Organoboron chemistry § Borates</a></p>
<p><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 trifluoroborate salts K[RBF3].
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<h2 id="reactivity">Reactivity</h2>
<p>Organotrifluoroborates are strong nucleophiles and react with electrophiles without transition-metal catalysts.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a>
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<h2 id="mechanism">Mechanism</h2>
<p>The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid <i>in situ</i>, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a>
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<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>"Alfa Aesar – Product Flyers & Technical Reviews – Organotrifluoroborates" (PDF). <a href="http://www.alfa.com/en/docs/Organotrifluoroborates.pdf" target="_blank">http://www.alfa.com/en/docs/Organotrifluoroborates.pdf</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>"Sigma-Aldrich – Chemical Synthesis – Technology Spotlights – Organotrifluoroborates". 2012-09-09. Archived from the original on 2012-09-09. <a href="https://archive.today/20120909074142/http://www.sigmaaldrich.com/chemistry/chemical-synthesis/technology-spotlights/organotrifluoroborates.html" target="_blank">https://archive.today/20120909074142/http://www.sigmaaldrich.com/chemistry/chemical-synthesis/technology-spotlights/organotrifluoroborates.html</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>Darses, Sylvain; Genet, Jean-Pierre (2008). "Potassium Organotrifluoroborates: New Perspectives in Organic Synthesis". Chemical Reviews. 108 (1): 288–325. doi:10.1021/cr0509758. PMID 18095714. <a href="/wiki/Chemical_Reviews" target="_blank">/wiki/Chemical_Reviews</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
<li id="fn:4"><p>Molander, Gary A.; Ellis, Noel (2007). "Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction". Accounts of Chemical Research. 40 (4): 275–286. doi:10.1021/ar050199q. PMID 17256882. <a href="/wiki/Accounts_of_Chemical_Research" target="_blank">/wiki/Accounts_of_Chemical_Research</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li>
<li id="fn:5"><p>Conole, G.; Clough, A.; Whiting, A. (1995). "Potassium Trifluorophenylborate". Acta Crystallogr. C. 51 (6): 1056–1059. doi:10.1107/S0108270194014198. <a href="/wiki/Acta_Crystallographica" target="_blank">/wiki/Acta_Crystallographica</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li>
<li id="fn:6"><p>Conole, G.; Clough, A.; Whiting, A. (1995). "Potassium Trifluorophenylborate". Acta Crystallogr. C. 51 (6): 1056–1059. doi:10.1107/S0108270194014198. <a href="/wiki/Acta_Crystallographica" target="_blank">/wiki/Acta_Crystallographica</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li>
<li id="fn:7"><p>Berionni, G.; Maji, B.; Knochel, P.; Mayr, H. (2012). "Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds". Chemical Science. 3 (3): 878–882. doi:10.1039/C2SC00883A. <a href="/wiki/Chemical_Science_(journal)" target="_blank">/wiki/Chemical_Science_(journal)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li>
<li id="fn:8"><p>Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. (2010). "Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride". Angew. Chem. Int. Ed. 49 (30): 5156–60. doi:10.1002/anie.201001522. PMID 20544767. <a href="/wiki/Angewandte_Chemie" target="_blank">/wiki/Angewandte_Chemie</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li>
<li id="fn:9"><p>"Mechanism Of Suzuki-Miyaura Coupling Revealed". Chemical & Engineering News. Retrieved 2010-06-27. <a href="http://pubs.acs.org/isubscribe/journals/cen/88/i26/html/8826scic6.html" target="_blank">http://pubs.acs.org/isubscribe/journals/cen/88/i26/html/8826scic6.html</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li>
</ol>

Organotrifluoroborate open-in-new

Organotrifluoroborate