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. 2010 Dec 15;132(49):17402-4.
doi: 10.1021/ja109120n. Epub 2010 Nov 18.

Palladium-catalyzed asymmetric synthesis of allylic fluorides

Matthew H Katcher  1 , Abigail G Doyle
Affiliations

Palladium-catalyzed asymmetric synthesis of allylic fluorides

Matthew H Katcher et al. J Am Chem Soc. .

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.

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