title: Regio- and stereoselective allylic trifluoromethylation and fluorination using CuCF3 and CuF reagents.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
authors.forename: Johanna M
authors.initials: JM
authors.lastname: Larsson
authors.forename: Stalin R
authors.initials: SR
authors.lastname: Pathipati
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó
mesh_terms: D003300:Copper / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; C519478:trifluoromethylcopper; C057829:copper fluoride; D003300:Copper; D005459:Fluorides