Photocatalytic decarboxylative alkylations of C(sp^(3))–H and C(sp^(2))–H bonds enabled by ammonium iodide in amide solvent  

作　　者：Guang-Zu Wang Ming-Chen Fu Bin Zhao Rui Shang 

机构地区：[1]Department of Chemistry,University of Science and Technology of China,Hefei 230026,China [2]Department of Chemistry,School of Science,The University of Tokyo,7-3-1 Hongo,Bunkyo-ku,Tokyo 113-0033,Japan

出　　处：《Science China Chemistry》2021年第3期439-444,共6页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(GG2065010002)and KY(2060000119);support from the Fundamental Research Funds for the Central Universities(WK2060120003);Anhui Provincial Natural Science Foundation(1908085QB53)。

摘　　要：A simple ammonium iodide salt in amide solvent catalyzes regioselective decarboxylative alkylation of C(sp^(3))-H bonds of Naryl glycine derivatives, of C(sp^(2))-H bond of heteroarenes, and cascade radical addition to unsaturated bond followed by intramolecular addition to arene, with a broad scope of N-hydroxyphthalimide derived redox active esters under visible light irradiation. The reactions are suggested to proceed through photoactivation of a transiently assembled chromophore from electron-deficient phthalimide moiety and iodide anion through an anion-π interaction in solvent cage followed by diffusion to generate solvated free radical species to react with C-H substrates. The simplicity, practicality, and broad substrate scope of this method highlight the synthetic power of photocatalysis through transiently assembled chromophore, and will hopefully inspire further developments of low cost photocatalysis based on various non-covalent interactions, which are prevalent in supramolecular chemistry and biosystems, for sustainable organic synthesis.

关 键 词：decarboxylative alkylation transiently assembled chromophore anion-πinteraction ammonium iodide solvent cage 

分 类 号：O621.251[理学—有机化学]