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Chemoselective Boronic Ester Synthesis by Controlled Speciation
Author(s) -
Fyfe James W. B.,
Seath Ciaran P.,
Watson Allan J. B.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406714
Subject(s) - pinacol , boronic acid , chemistry , aryl , palladium , suzuki reaction , combinatorial chemistry , catalysis , organic chemistry , alkyl
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross‐coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp 2 ‐hybridized boronic esters.