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Copper-catalyzed ?-boration of ?,?-unsaturated carbonyl compounds with tetrahydroxydiborane.

ABSTRACT: The copper-catalyzed ?-boration of ?,?-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary ?,?-unsaturated amides are converted to the corresponding ?-trifluoroboratoamides in good to excellent yields. The ?-boration of a variety of ?,?-unsaturated esters and ketones is also reported.

SUBMITTER: Molander GA 

PROVIDER: S-EPMC3162992 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane.

Molander Gary A GA   McKee Silas A SA  

Organic letters 20110805 17

The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported. ...[more]

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