Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 49, Pages 17402-17404Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja109120n
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- Princeton University
- Eli Lilly
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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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