4.8 Article

Activation of 1,1-difluoro-1-alkenes with a transition-metal complex: Palladium(II)-catalyzed Friedel-Crafts-type cyclization of 4,4-(difluorohomoallyl)arenes

Journal

ORGANIC LETTERS
Volume 9, Issue 22, Pages 4639-4642

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol702279w

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Cationic palladium(II) ([Pd(MeCN)(4)](BF4)(2)) provides the first transition-metal-catalyzed method for electrophilic activation of electron-deficient 1,1-difluoro-1-alkenes, which allows their Friedel-Crafts-type cyclization with an intramolecular aryl group via a Wacker-type process. By using BF3 center dot OEt2, the cyclization was effected by a catalytic amount of the palladium without its reoxidation.

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