Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse (Z)-1,2-bis(arylthio)alkene derivatives

An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes and arylhydrazines with sodium thiosulfate (Na2S2O3) as the sulfur source for the assembly of functionalized (Z)-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl-2 as the catalyst, a wide range of terminal alkynes and arylhydrazines are well tolerated, thus producing the desired products in good yields with good functional group tolerance and excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications in organic synthesis and material science.

Automated summary

This study introduces an efficient palladium-catalyzed three-component cascade bisthiolation method using sodium thiosulfate as the sulfur source for the synthesis of functionalized (Z)-1,2-bis(arylthio)alkene derivatives. The catalyst IPr-Pd-Im-Cl-2 showed good tolerance towards a wide range of terminal alkynes and arylhydrazines, leading to high yields and excellent regioselectivity in the desired products. Furthermore, the protocol is scalable and shows potential applications in organic synthesis and material science.