One-pot homologation of boronic acids: a platform for diversity-oriented synthesis

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: a platform for diversity-oriented synthesis

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

Pure And Applied Chemistry

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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.

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

Keywords

boronic acids
chemical reactivity
organometallic reagents

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10.1021/acs.orglett.5b03030

Muir-etal-OL-2015-One-pot-homologation-of-boronic-acids-a-platform-for-diversityFinal published version, 723 KBLicence: CC BY 4.0

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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.",

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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.

PY - 2015/12/3

Y1 - 2015/12/3

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

UR - http://pubs.acs.org/loi/orlef7

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DO - 10.1021/acs.orglett.5b03030

M3 - Article

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SP - 6030

EP - 6033

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

One-pot homologation of boronic acids: a platform for diversity-oriented synthesis

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Keywords

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