title: Chemoselective Suzuki-Miyaura Cross-Coupling via Kinetic Transmetallation.
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.
authors.affiliation: Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: James W B
authors.initials: JW
authors.lastname: Fyfe
authors.affiliation: GlaxoSmithKline, Medicines Research Centre, Stevenage, SG1 2NY, UK.
authors.forename: Neal J
authors.initials: NJ
authors.lastname: Fazakerley
authors.affiliation: Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK.
authors.forename: Allan J B
authors.identifier: 0000-0002-1582-4286
authors.initials: AJ
authors.lastname: Watson
keywords: boron; chemoselectivity; cross-coupling; palladium; transmetallation