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.
ORCID iDs
Fyfe, James W. B.
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Item type: Article ID code: 58949 Dates: DateEvent2 December 2016Published2 December 2016AcceptedNotes: This is the peer reviewed version of the following article: Fyfe, J. W. B., Fazakerley, N. J., & Watson, A. J. B. (2016). Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition, which will be published in final form at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. Keywords: multinucleophile systems, chemical synthesis, chemoselectivity, organoborons, arylboron nucleophiles, transmetallation, kinetic discrimination, Suzuki-Miyaura reaction, boron, cross-coupling, palladium, Chemistry, Chemistry(all) Subjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 05 Dec 2016 09:40 Last modified: 18 Mar 2023 04:00 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/58949
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