Open AccessSimple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
Author(s) -
Kai Hong,
Xun Liu,
James P. Morken
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja505455z
Subject(s) - chemistry , carbanion , umpolung , alkylation , alkoxide , alkyl , halide , boron , organic chemistry , organic synthesis , nucleophile , catalysis
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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