Effect of a Bidentate Phosphine Ligand on Palladium-Catalyzed Nucleophilic Substitution Reaction of Propargyl and Allyl Compounds with Thiols

摘要

Palladium-catalyzed nucleophilic substitution reactions of propargyl halides or mesylate 1 with thiols produce the propargyl and allenyl sulfides 2-9 in good yield.The yields of the coupling products were shown to be dependent on the phosphorus ligand(bidentate > monodentate)and on the nature of the solvent(DMF-d_7 > chloroform-d > benzene-d_6),thus indicating that the cationic eta~3-allenyl/propargylpalladium complex may be an important intermediate in this reaction.In addition,a similar effect was observed in the reaction of the allyl halide