Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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

Research output: Contribution to journal › Article

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.
LanguageEnglish
Number of pages5
JournalAngewandte Chemie International Edition
Publication statusAccepted/In press - 2 Dec 2016

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Boronic Acids
Nucleophiles
Kinetics
Esters

Keywords

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

Cite this

Fyfe, J. W. B., Fazakerley, N. J., & Watson, A. J. B. (Accepted/In press). Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition.
Fyfe, James W. B. ; Fazakerley, Neal J. ; Watson, Allan J. B. / Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. In: Angewandte Chemie International Edition. 2016.
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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.",
keywords = "multinucleophile systems, chemical synthesis, chemoselectivity, organoborons, arylboron nucleophiles, transmetallation, kinetic discrimination, Suzuki-Miyaura reaction, boron, cross-coupling, palladium",
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Fyfe, JWB, Fazakerley, NJ & Watson, AJB 2016, 'Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation' Angewandte Chemie International Edition.

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

In: Angewandte Chemie International Edition, 02.12.2016.

Research output: Contribution to journal › Article

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 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

Y1 - 2016/12/2

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

T2 - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

ER -

Fyfe JWB, Fazakerley NJ, Watson AJB. Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition. 2016 Dec 2.

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