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Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes
Author(s) -
Novikov Roman A.,
Borisov Denis D.,
Tarasova Anna V.,
Tkachev Yaroslav V.,
Tomilov Yury V.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803541
Subject(s) - halide , chemistry , gallium , reactivity (psychology) , acceptor , selectivity , component (thermodynamics) , combinatorial chemistry , photochemistry , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , thermodynamics , condensed matter physics
A new strategy for the three‐component addition of halide anions and acetylenes to donor–acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1,2‐zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail.