Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)
摘要
While the addition of C1-Lewis base enolates to carbonyls and related structures are well established, the related addition to thiocarbonyls compounds are unknown. Herein, we report a reaction cascade in which a C1-pyridinium enolate undergos addition to dithioesters, trithiocarbonates and xanthates. The reaction provides access to a range of dihydrothiophenes and dihydrothiopyrans (28-examples). Mechanistic investigations, including isolation of intermediates, electronic correlation, and kinetic isotope effect studies support the viability of an activated acid intermediate giving rise to the C1-pyridinium enolate which undergoes turnover limiting cyclization. Subsequent formation of a beta-thiolactone regenerates the catalyst with loss of carbon oxysulfide providing the observed products.
更多查看译文
关键词
Heterocycles, Lewis Base, Reaction Mechanisms, Thiocarbonyls, Thiophenes
AI 理解论文
溯源树
样例
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要