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Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42-  ( SCI-EXPANDED收录)  

文献类型:期刊文献

英文题名:Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42-

作者:Zhang, Ling[1,2];Fu, Youtian[1,2];Shen, Yi[1,2];Liu, Chengyu[1,2];Sun, Maolin[3];Cheng, Ruihua[3];Zhu, Weiping[4];Qian, Xuhong[4];Ma, Yueyue[3];Ye, Jinxing[1,2,3]

机构:[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Guangdong Univ Technol, Sch Biomed & Pharmaceut Sci, Guangzhou 510006, Peoples R China;[4]East China Univ Sci & Technol, Sch Pharm, State Key Lab Bioreactor Engn, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份:2022

卷号:13

期号:1

外文期刊名:NATURE COMMUNICATIONS

收录:;WOS:【SCI-EXPANDED(收录号:WOS:000826150900007)】;

基金:This work was partially sponsored by the National Natural Science Foundation of China (22071056, J.Y.; 22001070, Y.M.), and Shanghai Sailing Program (20YF1410400, Y.M.).

语种:英文

摘要:By merging electricity with sulfate, the Ritter-type amination of C(sp(3))-H bonds is developed in an undivided cell under room temperature. This method features broad substrate generality (71 examples, up to 93% yields), high functional-group compatibility, facile scalability, excellent site-selectivity and mild conditions. Common alkanes and electron-deficient alkylbenzenes are viable substrates. It also provides a straightforward protocol for incorporating C-deuterated acetylamino group into C(sp(3))-H sites. Application in the synthesis or modification of pharmaceuticals or their derivatives and gram-scale synthesis demonstrate the practicability of this method. Mechanistic experiments show that sulfate radical anion, formed by electrolysis of sulfate, served as hydrogen atom transfer agent to provide alkyl radical intermediate. This method paves a convenient and flexible pathway for realizing various synthetically useful transformations of C(sp(3))-H bonds mediated by sulfate radical anion generated via electrochemistry. The amination of C(sp3)-H bonds is an appealing and challenging task in organic synthesis. Here, by using an electrogenerated sulfate radical an HAT agent, the authors report a practical Ritter-type amination of C(sp3)-H bonds.

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