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Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

ABSTRACT: The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

SUBMITTER: Hong K

PROVIDER: S-EPMC4353009 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Hong Kai K Liu Xun X Morken James P JP

Journal of the American Chemical Society 20140716 30

The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion. ...[more]

PMID: 25019925

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