Transition-Metal-Catalyzed Reactions of Propargylamine with Carbon Dioxide and Carbon Disulfide

Abstract

The reactions of propargylamine derivatives with carbon dioxide and carbon disulfide have been systematically examined in the presence of transition-metal catalysts. Pd(OAc)(2) is the best catalyst for the formation of the corresponding oxazolidinones. In addition, we found that, in the reaction of propargylamine with carbon dioxide catalyzed by palladium(0) metal catalyst in toluene, both oxazolidinone 1 and imidazolidinone 2 could be obtained under mild reaction conditions at the same time. The reaction of 1 with primary and secondary amines has been examined. A plausible reaction mechanism for the formation of 2 was proposed. In addition, in this paper, we first disclosed the ligand's effect on this reaction. Using PBu(t)(3) as a ligand with Pd(2)(dba)(3), 1 was exclusively formed in 90% yield.