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

Pure And Applied Chemistry

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62 Citations (Scopus)

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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
Pages (from-to)	1249-1253
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	5
Early online date	16 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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Fyfe-etal-ACIE2016-Chemoselective-Suzuki-Miyaura-cross-coupling-via-kinetic-transmetallationAccepted author manuscript, 851 KB

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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.\}",

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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

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 5

ER -

Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation

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