Bis(1‐Methyl‐ortho‐Carboranyl)Borane

The Lewis superacid, bis(1‐methyl‐ortho‐carboranyl)borane, is rapidly accessed in two steps. It is a very effective hydroboration reagent capable of B−H addition to alkenes, alkynes, and cyclopropanes. To date, this is the first identified Lewis superacidic secondary borane and most reactive neutral...

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Bibliographic Details
Published inAngewandte Chemie Vol. 135; no. 34
Main Authors Akram, Manjur O., Tidwell, John R., Dutton, Jason L., Martin, Caleb D.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 21.08.2023
Subjects
Alkenes
Alkynes
Borane
Boranes
Carborane
Chemistry
Cyclopropane
Hydroboration
Lewis Acid
Organic compounds
Reagents
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Summary:The Lewis superacid, bis(1‐methyl‐ortho‐carboranyl)borane, is rapidly accessed in two steps. It is a very effective hydroboration reagent capable of B−H addition to alkenes, alkynes, and cyclopropanes. To date, this is the first identified Lewis superacidic secondary borane and most reactive neutral hydroboration reagent. A Lewis superacidic secondary borane, bis(ortho‐carboranyl)borane (HBMeoCb2) has been synthesized and is demonstrated to be a very reactive hydroboration reagent. It can perform regioselective 1,2‐hydroboration of carbon‐carbon multiple bonds, a unique 1,1‐hydroboration for acetylenes featuring an aryl and silyl substituent, and the formal 1,3‐hydroboration of cyclopropanes, all without the need of a catalyst.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202307040