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. 2014 Jul 30;136(30):10581-4.
doi: 10.1021/ja505455z. Epub 2014 Jul 16.

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

Kai Hong  1 , Xun Liu, James P Morken
Affiliations

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

Kai Hong et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1. Utility of α-Boryl Carbanions
Scheme 2
Scheme 2. Generation of α-Boryl Carbanions by Deborylation versus Deprotonation
Scheme 3
Scheme 3. Deborylative Alkylation for the Construction of Phenethylamine Building Blocks
Scheme 4
Scheme 4. Mechanistic Analysis of Deborylative Alkylation of Geminal Bis(boronates)
Scheme 5
Scheme 5. 13C-NMR Analysis of Deborylative Alkylation
See this image and copyright information in PMC

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