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Sequential Reactions of Trimethylstannyl Anions with Vinyl Chlorides and Dichlorides by the S RN 1 Mechanism Followed by Palladium-Catalyzed Cross-Coupling Processes

2004; American Chemical Society; Volume: 69; Issue: 19 Linguagem: Inglês

10.1021/jo049287z

1520-6904

Eduardo F. Córsico, Roberto A. Rossi,

Catalytic Alkyne Reactions

The reactions of trimethylstannyl ions (Me(3)Sn(-)) with vinyl chlorides in liquid ammonia give good yields of vinylstannanes. Some of them react in the dark, and others need light stimulation to react. The fact that these reactions are inhibited by radical and radical anion traps shows that they occur by the S(RN)1 mechanism. When the reaction takes place with 1,1-dichloro-1-alkenes, monosubstitution reduced products are formed in an E/Z mixture. The efficient synthesis of triarylolefins by Pd(0)-catalyzed cross-coupling reactions of vinylstannanes with several iodoarenes is reported. Similar yields were obtained in one-pot-type reactions.