Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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

Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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

Pure And Applied Chemistry

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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.

Original language	English
Number of pages	5
Journal	Angewandte Chemie International Edition
Publication status	Accepted/In press - 2 Dec 2016

Keywords

multinucleophile systems
chemical synthesis
chemoselectivity
organoborons
arylboron nucleophiles
transmetallation
kinetic discrimination
Suzuki-Miyaura reaction
boron
cross-coupling
palladium

Access to Document

Fyfe-etal-ACIE2016-Chemoselective-Suzuki-Miyaura-cross-coupling-via-kinetic-transmetallationAccepted author manuscript, 851 KB

http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

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@article{dc82ff749af7405a90078eb7881739d8,

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.",

keywords = "multinucleophile systems, chemical synthesis, chemoselectivity, organoborons, arylboron nucleophiles, transmetallation, kinetic discrimination, Suzuki-Miyaura reaction, boron, cross-coupling, palladium",

author = "Fyfe, {James W. B.} and Fazakerley, {Neal J.} and Watson, {Allan J. B.}",

note = "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.",

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AU - Fyfe, James W. B.

AU - Fazakerley, Neal J.

AU - Watson, Allan J. B.

N1 - 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.

PY - 2016/12/2

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N2 - 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.

AB - 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.

KW - multinucleophile systems

KW - chemical synthesis

KW - chemoselectivity

KW - organoborons

KW - arylboron nucleophiles

KW - transmetallation

KW - kinetic discrimination

KW - Suzuki-Miyaura reaction

KW - boron

KW - cross-coupling

KW - palladium

UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

M3 - Article

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

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