Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 39, Pages 16859-16872Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008096
Keywords
1; 2-migration; boronate complex; cross-coupling; electrophiles; stereospecific
Categories
Funding
- DFG [442129649]
- H2020 ERC [670668]
- Engineering and Physical Sciences Research Council [EP/L011999/1] Funding Source: researchfish
- EPSRC [EP/L011999/1] Funding Source: UKRI
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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 alpha-leaving group, oxidation of an alpha-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.
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