可见光诱导的磷酰重氮甲基芳烃与吡啶鎓1,4-两性离子硫醇盐的[1+5]环化反应
Visible-Light-Induced [1+5] Annulation of Phosphoryl Diazomethylarenes and Pyridinium 1,4-Zwitterionic Thiolates.
作者信息
Sun Simin, Wei Yuliang, Xu Jiaxi
机构信息
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.
出版信息
Org Lett. 2022 Aug 19;24(32):6024-6030. doi: 10.1021/acs.orglett.2c02321. Epub 2022 Aug 11.
Visible-light-induced [1+5] annulation of phosphoryl diazomethylarenes and pyridinium 1,4-zwitterionic thiolates generates various trifunctionalized dialkyl 1-phosphoryl-1,9a-dihydropyrido[2,1-][1,4]thiazine-3,4-dicarboxylates in good to excellent yields and diastereoselectivities. The annulation involves the nucleophilic attack of thiolates on diazomethylarene-generated carbenes followed by an intramolecular cyclization, is free of catalysts, is atom-economical, and has mild reaction conditions.
可见光诱导的磷酰基重氮甲基芳烃与吡啶鎓1,4-两性离子硫醇盐的[1+5]环化反应以良好至优异的产率和非对映选择性生成了各种三官能化的二烷基1-磷酰基-1,9a-二氢吡啶并[2,1-][1,4]噻嗪-3,4-二羧酸盐。该环化反应涉及硫醇盐对重氮甲基芳烃生成的卡宾的亲核进攻，随后进行分子内环化，无需催化剂，原子经济性高，且反应条件温和。
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