1258495-63-4Relevant academic research and scientific papers
Regio- and stereoselective allylic trifluoromethylation and fluorination using CuCF3 and CuF reagents
Larsson, Johanna M.,Pathipati, Stalin R.,Szabo, Kalman J.
, p. 7330 - 7336 (2013/08/23)
Copper-mediated trifluoromethylation of allylic chlorides and trifluoroacetates was performed using a convenient Cu-CF3 reagent. The reaction is suitable for selective synthesis of allyl trifluoromethyl species. Mechanistic studies indicate that the reaction proceeds via a nucleophilic substitution mechanism involving allyl copper intermediates. The analogous Cu-F reagent was suitable for fluorination of allyl chlorides. Stereodefined cyclic substrates reacted regio- and stereoselectively.
Palladium-catalyzed asymmetric synthesis of allylic fluorides
Katcher, Matthew H.,Doyle, Abigail G.
supporting information; experimental part, p. 17402 - 17404 (2011/02/23)
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 SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.
