alpha- and beta-Stannyl Trifluoromethylbutenoates: Regioselective Preparation and Use in Copper(I)-Catalyzed Allylation and Propargylation Reactions

作者：Carcenac Yvan; Zine Khalid; Kizirian Jean Claude; Thibonnet Jerome; Duchene Alain; Parrain Jean Luc^*; Abarbri Mohamed

来源：Advanced Synthesis & Catalysis, 2010, 352(6): 949-954.

DOI：10.1002/adsc.200900828

• allylation
• copper(I)-catalyzed cross coupling
• ethyl trifluorobutynoate
• propargylation
• regioselective
• hydrostannylation

The palladium-free hydrostannylation of ethyl 4,4,4-trifluorobutynoate 1 with tributyltin hydride at room temperature is highly regio- and stereoselective, providing good yields of beta-trifluoromethyl (Z)-alpha- or (Z)-beta-stannylacrylates 2. Vinyl-stannanes 2 undergo a copper(1)-catalyzed coupling reactions with allylic or propargylic bromides leading selectively to good yields of the corresponding allylated or propargylated products without allylic or allenic transposition.

• 出版日期2010-4