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Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

ABSTRACT: The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

SUBMITTER: Molander GA

PROVIDER: S-EPMC3407959 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Molander Gary A GA Trice Sarah L J SL Kennedy Steven M SM Dreher Spencer D SD Tudge Matthew T MT

Journal of the American Chemical Society 20120706 28

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthe ...[more]

PMID: 22769742

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