Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control

Ciaran P. Seath; James W. B. Fyfe; John J. Molloy; Allan J. B. Watson

doi:10.1002/ange.201504297

Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control

Ciaran P. Seath, James W. B. Fyfe, John J. Molloy, Allan J. B. Watson

Pure And Applied Chemistry

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Abstract

Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki-Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetallation, this enables chemoselective formation of two C-C bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.

Original language	English
Pages (from-to)	9976-9979
Number of pages	4
Journal	Angewandte Chemie
Volume	54
Issue number	34
Early online date	1 Jul 2015
DOIs	https://doi.org/10.1002/ange.201504297
Publication status	Published - 17 Aug 2015

Keywords

boron
chemoselectivity
cross-coupling
palladium
speciation

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Seath-etal-AC-2015-Tandem-chemoselective-Suzuki-Miyaura-cross-coupling-enabled-by-nucleophileAccepted author manuscript, 782 KB

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abstract = "Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki-Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetallation, this enables chemoselective formation of two C-C bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.",

keywords = "boron, chemoselectivity, cross-coupling, palladium, speciation",

author = "Seath, \{Ciaran P.\} and Fyfe, \{James W. B.\} and Molloy, \{John J.\} and Watson, \{Allan J. B.\}",

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AU - Seath, Ciaran P.

AU - Fyfe, James W. B.

AU - Molloy, John J.

AU - Watson, Allan J. B.

N1 - This is the peer reviewed version of the following article: Seath, C. P., Fyfe, J. W. B., Molloy, J. J., & Watson, A. J. B. (2015). Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control. Angewandte Chemie, which has been published in final form at http://www.dx.doi.org/10.1002/ange.201504297. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving

PY - 2015/8/17

Y1 - 2015/8/17

N2 - Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki-Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetallation, this enables chemoselective formation of two C-C bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.

AB - Control of boronic acid speciation is presented as a strategy to achieve nucleophile chemoselectivity in the Suzuki-Miyaura reaction. Combined with simultaneous control of oxidative addition and transmetallation, this enables chemoselective formation of two C-C bonds in a single operation, providing a method for the rapid preparation of highly functionalized carbogenic frameworks.

KW - boron

KW - chemoselectivity

KW - cross-coupling

KW - palladium

KW - speciation

UR - http://onlinelibrary.wiley.com/journal/10.1002/%28ISSN%291521-3757

U2 - 10.1002/ange.201504297

DO - 10.1002/ange.201504297

M3 - Article

SN - 0044-8249

VL - 54

SP - 9976

EP - 9979

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 34

ER -

Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control

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Keywords

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