One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis

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 medicina...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 24; pp. 6030 - 6033
Main Authors Muir, Calum W., Vantourout, Julien C., Isidro-Llobet, Albert, Macdonald, Simon J. F., Watson, Allan J. B.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.12.2015
Amer Chemical Soc
Subjects
Boronic Acids - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Science & Technology
PALLADIUM-CATALYZED BORYLATION
BUILDING-BLOCKS
ESTERS
ARENES
CROSS-COUPLING MODULES
C-H BORYLATION
SPECIATION CONTROL
DERIVATIVES
ARYL CHLORIDES
SMALL-MOLECULE SYNTHESIS
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Summary: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.
Bibliography:researchfish
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03030