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Chemoselective boronic ester synthesis via controlled speciation

Fyfe, James W. B. and Seath, Ciaran P. and Watson, Allan J. B. (2014) Chemoselective boronic ester synthesis via controlled speciation. Angewandte Chemie, 53 (45). 12077–12080. ISSN 0044-8249

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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 Pd catalyst also facilitates streamlined iterative catalytic C-C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.