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Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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Author(s)

James W. B. Fyfe, Neal J. Fazakerley, Allan J. B. Watson

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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.
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Original languageEnglish
Pages (from-to)1249-1253
JournalAngewandte Chemie International Edition
Volume56
Issue number5
Early online date2 Dec 2016
DOIs
Publication statusPublished - 24 Jan 2017

    Research areas

  • Multinucleophile systems, Chemical synthesis, Chemoselectivity, Organoborons, Arylboron nucleophiles, Transmetallation, Kinetic discrimination, Suzuki-Miyaura reaction, Boron, Cross-coupling, Palladium

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