Chemoselective boronic ester synthesis via controlled speciation

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

doi:10.1002/anie.201406714

Chemoselective boronic ester synthesis via controlled speciation

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

School of Chemistry

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

Abstract

Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active Pd catalyst also facilitates streamlined iterative catalytic C—C bond formation and provides a method for the controlled oligomerization of sp²-hybridized boronic esters.

Original language	English
Pages (from-to)	12077-12080
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	53
Issue number	45
DOIs	https://doi.org/10.1002/anie.201406714
Publication status	Published - 3 Nov 2014

Keywords

Chemoselectivity
Boron
Boronic acid solution speciation
Cross-coupling
Palladium
Boronic ester
Oligomerization

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10.1002/anie.201406714Licence: CC BY

Fyfe_2014_ACIE_Boronic_CC
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 467 KBLicence: CC BY

Cite this

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abstract = "Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active Pd catalyst also facilitates streamlined iterative catalytic C—C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.",

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doi = "10.1002/anie.201406714",

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T1 - Chemoselective boronic ester synthesis via controlled speciation

AU - Fyfe, James W. B.

AU - Seath, Ciaran P.

AU - Watson, Allan J. B.

PY - 2014/11/3

Y1 - 2014/11/3

N2 - Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active Pd catalyst also facilitates streamlined iterative catalytic C—C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.

AB - Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active Pd catalyst also facilitates streamlined iterative catalytic C—C bond formation and provides a method for the controlled oligomerization of sp2-hybridized boronic esters.

KW - Chemoselectivity

KW - Boron

KW - Boronic acid solution speciation

KW - Cross-coupling

KW - Palladium

KW - Boronic ester

KW - Oligomerization

UR - https://www.scopus.com/pages/publications/84911460873

U2 - 10.1002/anie.201406714

DO - 10.1002/anie.201406714

M3 - Article

SN - 1433-7851

VL - 53

SP - 12077

EP - 12080

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 45

ER -

Chemoselective boronic ester synthesis via controlled speciation

Abstract

Keywords

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