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Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles
Author(s) -
Wang Hui,
Jing Changcheng,
Noble Adam,
Aggarwal Varinder Kumar
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008096
Subject(s) - electrophile , stereospecificity , chemistry , combinatorial chemistry , boron , catalysis , stereochemistry , computational chemistry , organic chemistry
The stereospecific 1,2‐migration of boronate complexes is one of the most representative reactions in boron chemistry. This process has been used extensively to develop powerful methods for asymmetric synthesis, with applications spanning from pharmaceuticals to natural products. Typically, 1,2‐migration of boronate complexes is driven by displacement of an α‐leaving group, oxidation of an α‐boryl radical, or electrophilic activation of an alkenyl boronate complex. The aim of this article is to summarize the recent advances in the rapidly expanding field of electrophile‐induced stereospecific 1,2‐migration of groups from boron to sp 2 and sp 3 carbon centers. It will be shown that three different conceptual approaches can be utilized to enable the 1,2‐migration of boronate complexes: stereospecific Zweifel‐type reactions, catalytic conjunctive coupling reactions, and transition metal‐free sp 2 –sp 3 couplings. A discussion of the reaction scope, mechanistic insights, and synthetic applications of the work described is also presented.