Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 45, Pages 12077-12080Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406714
Keywords
boron; chemoselectivity; cross-coupling; oligomerization; palladium
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Funding
- EPSRC
- EPSRC UK National Mass Spectrometry Facility at Swansea University
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council [1628052] Funding Source: researchfish
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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 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.
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