Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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

doi:10.1002/anie.201610797

Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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
Pages (from-to)	1249-1253
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	5
Early online date	2 Dec 2016
DOIs	https://doi.org/10.1002/anie.201610797
Publication status	Published - 24 Jan 2017

Keywords

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

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10.1002/anie.201610797

https://strathprints.strath.ac.uk/id/eprint/58949

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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 work was supported by the EPSRC. We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses and GlaxoSmithKline for PhD studentship (J.W.B.F.) along with financial support and chemical resources. ",

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doi = "10.1002/anie.201610797",

language = "English",

volume = "56",

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journal = "Angewandte Chemie International Edition",

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T1 - Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

AU - Fyfe, James W. B.

AU - Fazakerley, Neal J.

AU - Watson, Allan J. B.

N1 - This work was supported by the EPSRC. We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses and GlaxoSmithKline for PhD studentship (J.W.B.F.) along with financial support and chemical resources.

PY - 2017/1/24

Y1 - 2017/1/24

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

U2 - 10.1002/anie.201610797

DO - 10.1002/anie.201610797

M3 - Article

SN - 1433-7851

VL - 56

SP - 1249

EP - 1253

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 5

ER -

Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

Abstract

Keywords

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