Metal-Free Photocatalytic[4+2]Annulation of Acrylamides with 2-Benzyl-2-bromocarbonyls to Assemble Tetralin-1-carboxamides  

作　　者：Weicai Li Lu Tan Yijun Chen Rui Liu Zhongyu Qi Shixuan Yuan Zhanwen Huang Siping Wei Xi Du Dong Yi 

机构地区：[1]Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province,School of Pharmacy,Southwest Medical University,Luzhou,Sichuan 646000,China [2]Department of Chemistry,School of Basic Medical Science,Southwest Medical University,Luzhou,Sichuan 646000,China [3]Department of Pharmacy,Affiliated Hospital,Southwest Medical University,Luzhou,Sichuan 646000,China

出　　处：《Chinese Journal of Chemistry》2024年第2期157-163,共7页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.22101237,22171233);the Science and Technology Program of Sichuan Province(Nos.2022YFS0608,2022NSFSC1219);the Open Project Program of Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province(Nos.HYX21003,HYX22008);the research fund of Southwest Medical University(2021ZKMS042).

摘　　要：Tetralin-1-carboxamides are frequently incorporated in myriad medicinally important molecules.However,their existing synthetic routes not only suffer from some drawbacks such as tedious procedures,harsh reaction conditions,narrow substrate scope,low yields,and environmental problems,but are also based upon the elaboration of uneasily available non-linear tetralin derivatives.Herein,we describe a metal-and additive-free visible light-induced[4+2]annulation of two simple linear starting materials,namely acrylamides and 2-benzyl-2-bromocarbonyls,through a cascade C(sp^(3))-Br/C(sp^(2))-H bond cleavage,double C-C bond formation,and aromatization sequence.The developed protocol provides a convenient,efficient,and green approach to a variety of tetralin-1-carboxamide derivatives with good functional group compatibility.Importantly,the resulting products could also undergo the Licl-mediated mono-decarboxylative cyclization process to further furnish the architecturally novel bridged polycyclic imides with excellentcis-diastereoselectivities.

关 键 词：ANNULATION METAL-FREE Photoredox catalysis Tetralin-1-carboxamide Cyclic imides Synthetic methods C-C coupling Radical reactions Reaction mechanisms 

分 类 号：O62[理学—有机化学]