Hydroboration–oxidation reaction

Hydroboration–oxidation reaction is a two-step <a href="/facts/Hydration_reaction/T1Vb2u1d">hydration reaction</a> that converts an <a href="/facts/Alkene/RtYcS6kU">alkene</a> into an <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohol</a>. The process results in the <a href="/facts/Syn_and_anti_addition/EYjRTE4J">syn addition</a> of a hydrogen and a <a href="/facts/Hydroxyl/1Hs2QAEv">hydroxyl</a> group where the <a href="/facts/Double_bond/qDemMn0c">double bond</a> had been. Hydroboration–oxidation is an <a href="/facts/Markovnikov%2527s_rule/WJokRx6l">anti-Markovnikov</a> reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more <a href="/facts/Stereospecific/BT4em18V">stereospecific</a> and complementary <a href="/facts/Regiochemistry/m3Bs2Xzl">regiochemical</a> alternative to other hydration reactions such as <a href="/facts/Acid_catalysis/JkJ7LkT6">acid-catalyzed</a> addition and the <a href="/facts/Oxymercuration_reaction/xhf5hIDh">oxymercuration–reduction</a> process. The reaction was first reported by <a href="/facts/Herbert_C._Brown/gzHbbzR3">Herbert C. Brown</a> in the late 1950s and it was recognized in his receiving the <a href="/facts/Nobel_Prize_in_Chemistry/8Nb8Ajjy">Nobel Prize in Chemistry</a> in 1979.
The general form of the reaction is as follows:

<a href="/facts/Tetrahydrofuran/P5t6SkMK">Tetrahydrofuran</a> (THF) is the archetypal <a href="/facts/Solvent/LoMPMz8S">solvent</a> used for hydroboration.

Hydroboration–oxidation reaction open-in-new

Hydroboration–oxidation reaction