An efficient synthesis of α-thioenamine compounds via a K_(2)S_(2)O_(8)-promoted cross-dehydrogenative coupling reaction between heterocyclic thiols and enamine esters in an aqueous medium has been developed.The reac...An efficient synthesis of α-thioenamine compounds via a K_(2)S_(2)O_(8)-promoted cross-dehydrogenative coupling reaction between heterocyclic thiols and enamine esters in an aqueous medium has been developed.The reaction showed good tolerance for enamine esters and heterocyclic thiols with various functional groups,producingα-thioenamine derivatives in moderate to high yields.Mechanistic studies revealed that heterocyclic thiols react with K_(2)S_(2)O_(8) in water to form reactive disulfides in situ,which then react with enamine esters to generate a series ofα-thioenamines.Building on the proposed mechanism,we developed a sulfenylation reaction of enamine esters with disulfides without the need for an oxidant.This oxidant-free approach has been successfully employed to synthesize DNA-taggedα-thioenamine,demonstrating its considerable potential for various synthetic applications.展开更多
基金the financial support from the Key R&D Projects of Hainan Province(No.ZDYF2024SHFZ065)the Cultivation Research Foundation of Hainan Medical University(No.RZ2300002021 to Dulin Kong,No.RZ2400001591 to Guangkuan Zhao)the Postgraduate Innovation Project of Hainan Medical University(No.HYYB2023A07 to Wenyan Wei)。
文摘An efficient synthesis of α-thioenamine compounds via a K_(2)S_(2)O_(8)-promoted cross-dehydrogenative coupling reaction between heterocyclic thiols and enamine esters in an aqueous medium has been developed.The reaction showed good tolerance for enamine esters and heterocyclic thiols with various functional groups,producingα-thioenamine derivatives in moderate to high yields.Mechanistic studies revealed that heterocyclic thiols react with K_(2)S_(2)O_(8) in water to form reactive disulfides in situ,which then react with enamine esters to generate a series ofα-thioenamines.Building on the proposed mechanism,we developed a sulfenylation reaction of enamine esters with disulfides without the need for an oxidant.This oxidant-free approach has been successfully employed to synthesize DNA-taggedα-thioenamine,demonstrating its considerable potential for various synthetic applications.
