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Chemoselective Suzuki–Miyaura Cross‐Coupling via Kinetic Transmetallation
Author(s) -
Fyfe James W. B.,
Fazakerley Neal J.,
Watson Allan J. B.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201610797
Subject(s) - transmetalation , pinacol , nucleophile , chemistry , electrophile , boronic acid , coupling (piping) , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
Chemoselective Suzuki–Miyaura cross‐coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective cross‐couplings in a single operation in the absence of protecting groups.