Trifluoromethylation of propargylic halides and trifluoroacetates using (Ph3P)3Cu(CF3) reagent.
A copper-mediated trifluoromethylation of propargylic halides and trifluoroacetates was performed with high allenyl or propargyl selectivity. The reaction proceeds smoothly with aliphatic and aromatic substituents bearing either electron-withdrawing or -supplying groups. Preliminary mechanistic results indicate an ionic mechanism involving nucleophilic transfer of the CF(3) group from the Cu complex to the propargylic substrate.
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
Tony S N
TS
Zhao
Kálmán J
KJ
Szabó
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D000466:Alkadienes; D000480:Alkynes; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D003300:Copper; D014269:Trifluoroacetic Acid