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Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

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Bis(1-Methyl-ortho-Carboranyl)Borane.

Manjur O Akram¹, John R Tidwell¹, Jason L Dutton²

¹Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, TX, 76798, USA.

Angewandte Chemie (International Ed. in English)

|June 20, 2023

Summary

A new Lewis superacid, bis(1-methyl-ortho-carboranyl)borane, is synthesized quickly. This potent secondary borane acts as a highly reactive hydroboration reagent for various unsaturated compounds.

Keywords:

Borane Carborane Cyclopropane Hydroboration Lewis Acid

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Area of Science:

Organometallic Chemistry
Boron Chemistry

Background:

Lewis superacids are crucial catalysts in organic synthesis.
Secondary boranes are typically less reactive than primary boranes.

Purpose of the Study:

To synthesize a novel Lewis superacidic secondary borane.
To evaluate its efficacy as a hydroboration reagent.

Main Methods:

Two-step synthesis of bis(1-methyl-ortho-carboranyl)borane.
Testing its reactivity in hydroboration reactions with alkenes, alkynes, and cyclopropanes.

Main Results:

Rapid synthesis of the target compound was achieved.
Bis(1-methyl-ortho-carboranyl)borane demonstrated high effectiveness in B-H addition.
It is the first identified Lewis superacidic secondary borane.

Conclusions:

Bis(1-methyl-ortho-carboranyl)borane is a readily accessible and highly reactive hydroboration reagent.
This discovery expands the scope of Lewis superacids and secondary boranes in chemical synthesis.