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Palladium-catalyzed asymmetric synthesis of allylic fluorides.

Journal of the American Chemical Society (2010-11-23)
Matthew H Katcher, Abigail G Doyle
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.

MATERIALS
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Product Description

Sigma-Aldrich
Tris(dibenzylideneacetone)dipalladium(0), 97%