Chemoselective Suzuki-Miyaura Cross-Coupling via Kinetic Transmetallation
James W B Fyfe1, Neal J Fazakerley2, Allan J B Watson1
1Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
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.
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