Sequential reactions of trimethylstannyl anions with vinyl chlorides and dichlorides by the SRN1 mechanism followed by palladium-catalyzed cross-coupling processes

Article abstract of DOI:10.1021/jo049287z

The reactions of trimethylstannyl ions (Me₃Sn^-) 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_RN1 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.