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Palladium-catalyzed asymmetric synthesis of allylic fluorides.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2010 Dec 15; Vol. 132 (49), pp. 17402-4. Date of Electronic Publication: 2010 Nov 18. - Publication Year :
- 2010
-
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.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 132
- Issue :
- 49
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 21087003
- Full Text :
- https://doi.org/10.1021/ja109120n