Simultaneous Immobilization of CO₂ and H₂S by Propargyl Amines under Mild Conditions: Efficient Synthesis of Thiazolidine-2-ones

Abstract

A series of thiazolidine-2-one derivatives were synthesized by a three-component reaction of carbon dioxide, hydrogen sulfide, and propargyl amines under mild conditions. The simultaneous incorporation of carbon dioxide and hydrogen sulfide into the same organic product was realized. Moreover, a reaction mechanism was proposed based on the detailed NMR and FTIR study, which indicated that propargyl amine reacted with CO 2 first to form carbamate, followed by O/S exchange with H 2 S to form thiocarbamate and the final cyclization of thiocarbamate to form thiazolidine-2-one.

Integration of CO2capture, activation, and conversion with a ternary acetylglucosyl 2-methyl-imidazolium modified Pd catalyst

“…The target product 16m could be produced in a high yield when R 1 was an n-butyl group. 48 Fig. 1 Comparison with other reported catalysts.…”

Regioselective anti-Silyllithiation of Propargylic Amines

“…6 While regioselective syn-addition of silylmetals with either regioselectivity has been established in the presence of a transition metal catalyst, [6][7][8] anti-additions of silylmetals have been rarely reported. [9][10][11][12] In this context, we recently discovered the regioselective anti-addition of silyllithiums to propargylic alkoxides (Scheme 1A). 13 The reaction affords an alkenyllithium bearing a silyl group in the proximal position to the hydroxy group.…”