Photoredox-Catalyzed Metal-Free Regio-&Stereoselective C(sp^(2))-H Amination of Enamides with N-Aminopyridium Salts  

作　　者：Zheng-Bao Qin Kun Ni Li Wang Xiao-Di Wu Yu Zhang Kai Zhao 

机构地区：[1]Institute of Advanced Synthesis,School of Chemistry and Molecular Engineering,Jiangsu National Synergetic Innovation Center for Advanced Materials,Nanjing Tech University,Nanjing,Jiangsu211816,China [2]college of Chemical Engineering,Nanjing Forestry University,Nanjing,Jiangsu 210037,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2235-2242,共8页中国化学（英文版）

基　　金：the financial support from the National Natural Science Foundation of China(21801129,22078153 and 22378201);National Key Research and Development Program of China(2022YFB3805603);Natural Science Research Projects in Jiangsu Higher Education Institutions(18KJB150018);Nanjing Tech University(Start-up Grant Nos.39837137,39837101 and 3827401739)for financial support.

摘　　要：A visible-light-induced photoredox-catalyzed regioselective and stereoselective C(sp')-H amination of enamides with bench-stable and A visible-light-induced photoredox-catalyzed regioselective and stereoselective C(sp)-H amination of enamides with bench-stable and easily accessible N-aminopyridium salts is developed,affording synthetically and biologically prominent vicinal 1,2-diamine scaffolds with broad substrate scope and excellent functional group compatibility.The transformation proceeded through a radical pathway involving the Giese addition of the relatively electrophilic N-centered sulfonamidyl radical species to nucleophilicβ-olefinic position of enamides followed by the ensuing single electron oxidation andβ-H elimination,delivering geometrically-defined Z-configuredβ-sulfonamidylated enamides.The operational simplicity,environmental friendliness and cost efficiency of this methodology allowed it to pave a new avenue to enrich the arsenal of synthetically crucial functionalized enamides and their related derivatives.

关 键 词：ENAMIDES AMINATION Photoredox catalysis REGIOSELECTIVE STEREOSELECTIVE METAL-FREE 

分 类 号：O62[理学—有机化学]