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A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

ABSTRACT: A three-component coupling of vinyl triflates and boronic acids to alkenes catalyzed by palladium is reported. Using 1,3-dienes, selective 1,2-alkene difunction-alization is observed, whereas the use of terminal alkenes results in 1,1-alkene difunctionalization. The reaction outcome is attributed to the formation of stabilized, cationic Pd-?-allyl intermediates to regulate ?-hydride elimination.

SUBMITTER: Liao L

PROVIDER: S-EPMC3084658 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Liao Longyan L Jana Ranjan R Urkalan Kaveri Balan KB Sigman Matthew S MS

Journal of the American Chemical Society 20110330 15

A three-component coupling of vinyl triflates and boronic acids to alkenes catalyzed by palladium is reported. Using 1,3-dienes, selective 1,2-alkene difunction-alization is observed, whereas the use of terminal alkenes results in 1,1-alkene difunctionalization. The reaction outcome is attributed to the formation of stabilized, cationic Pd-π-allyl intermediates to regulate β-hydride elimination. ...[more]

PMID: 21449562

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