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Chemoselective boronic ester synthesis by controlled speciation.

ABSTRACT: 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 C-C bond formation and provides a method for the controlled oligomerization of sp(2) -hybridized boronic esters.

SUBMITTER: Fyfe JW 

PROVIDER: S-EPMC4501314 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Chemoselective boronic ester synthesis by controlled speciation.

Fyfe James W B JW   Seath Ciaran P CP   Watson Allan J B AJ  

Angewandte Chemie (International ed. in English) 20140929 45

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 C-C bond formation and provides a method for the controlled oligomerization  ...[more]

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