One-pot homologation of boronic acids

Calum W. Muir; Julien C. Vantourout; Albert Isidro-Llobet; Simon J. F. Macdonald; Allan J. B. Watson

doi:10.1021/acs.orglett.5b03030

One-pot homologation of boronic acids

Calum W. Muir, Julien C. Vantourout, Albert Isidro-Llobet, Simon J. F. Macdonald, Allan J. B. Watson

School of Chemistry

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

Abstract

Formal homologation of sp²-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

Original language	English
Pages (from-to)	6030-6033
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	24
Early online date	3 Dec 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b03030
Publication status	Published - 18 Dec 2015

Keywords

Boronic acids
Chemical reactivity
Organometallic reagents

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10.1021/acs.orglett.5b03030Licence: CC BY

Watson_2015_OL_One-pot_CC
© 2015 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 724 KBLicence: CC BY

Cite this

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abstract = "Formal homologation of sp2-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.",

keywords = "Boronic acids, Chemical reactivity, Organometallic reagents",

author = "Muir, {Calum W.} and Vantourout, {Julien C.} and Albert Isidro-Llobet and Macdonald, {Simon J. F.} and Watson, {Allan J. B.}",

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doi = "10.1021/acs.orglett.5b03030",

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AU - Muir, Calum W.

AU - Vantourout, Julien C.

AU - Isidro-Llobet, Albert

AU - Macdonald, Simon J. F.

AU - Watson, Allan J. B.

N1 - This work was supported by the Engineering and Physical Sciences Research Council (EPSRC).

PY - 2015/12/18

Y1 - 2015/12/18

N2 - Formal homologation of sp2-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

AB - Formal homologation of sp2-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

KW - Boronic acids

KW - Chemical reactivity

KW - Organometallic reagents

U2 - 10.1021/acs.orglett.5b03030

DO - 10.1021/acs.orglett.5b03030

M3 - Article

SN - 1523-7060

VL - 17

SP - 6030

EP - 6033

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

One-pot homologation of boronic acids

Abstract

Keywords

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