Journal of the American Chemical Society 2010-12-15

Palladium-catalyzed asymmetric synthesis of allylic fluorides.

Matthew H Katcher, Abigail G Doyle

Index: J. Am. Chem. Soc. 132 , 17402, (2010)

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Abstract

The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C-F bond formation occurs by an S(N)2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.