Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

Fyfe, James W. B. and Fazakerley, Neal J. and Watson, Allan J. B. (2016) Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition. ISSN 1433-7851 (In Press)

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    Abstract

    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.