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Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. / Fyfe, James W. B.; Fazakerley, Neal J.; Watson, Allan J. B.

In: Angewandte Chemie International Edition, Vol. 56, No. 5, 24.01.2017, p. 1249-1253.

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Fyfe, JWB, Fazakerley, NJ & Watson, AJB 2017, 'Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation', Angewandte Chemie International Edition, vol. 56, no. 5, pp. 1249-1253. https://doi.org/10.1002/anie.201610797

APA

Fyfe, J. W. B., Fazakerley, N. J., & Watson, A. J. B. (2017). Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition, 56(5), 1249-1253. https://doi.org/10.1002/anie.201610797

Vancouver

Fyfe JWB, Fazakerley NJ, Watson AJB. Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition. 2017 Jan 24;56(5):1249-1253. https://doi.org/10.1002/anie.201610797

Author

Fyfe, James W. B. ; Fazakerley, Neal J. ; Watson, Allan J. B. / Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. In: Angewandte Chemie International Edition. 2017 ; Vol. 56, No. 5. pp. 1249-1253.

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@article{961a910ddb834a0fb195f4fc8db77db5,
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. ",
year = "2017",
month = jan,
day = "24",
doi = "10.1002/anie.201610797",
language = "English",
volume = "56",
pages = "1249--1253",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons, Ltd.",
number = "5",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

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

VL - 56

SP - 1249

EP - 1253

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 5

ER -

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