In Situ Alkyl Radical Recycling-Driven Decoupled Electrophotochemical Deamination

被引:37
作者
Wang, Kui [1 ]
Liu, Xiaoyu [1 ]
Yang, Siyu [1 ]
Tian, Yan [1 ]
Zhou, Mingyang [1 ]
Zhou, Jianhua [1 ]
Jia, Xiaofei [2 ]
Li, Baoying [1 ]
Liu, Siyuan [1 ]
Chen, Jianbin [1 ]
机构
[1] Qilu Univ Technol, Sch Chem & Chem Engn, Shandong Prov Key Lab Mol Engn, State Key Lab Biobased Mat & Green Papermaking,Sh, Jinan 250353, Peoples R China
[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Key Lab Opt Elect Sensing & Analyt Chem Life Sci, MOE, Qingdao 266042, Peoples R China
基金
中国国家自然科学基金;
关键词
SALTS; GENERATION; CATALYSIS;
D O I
10.1021/acs.orglett.2c01022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Molecular electrophotocatalysis has emerged as a powerful strategy for the development of sustainable synthetic protocols. With the proof-of-concept, we exploited a versatile electrophotocatalytic deaminative alkylation approach. Mechanistic investigation indicated that in situ recycling of the alkyl radicals was the key point. Notably, ligand modification and late-stage functionalization of pharmaceuticals were also established, highlighting its feasibility in practical utilization.
引用
收藏
页码:3471 / 3476
页数:6
相关论文
共 31 条
[1]   Synthetic Photoelectrochemistry [J].
Barham, Joshua P. ;
Koenig, Burkhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :11732-11747
[2]   Recent advances in radical chemistry proceeding through pro-aromatic radicals [J].
Bhunia, Anup ;
Studer, Armido .
CHEM, 2021, 7 (08) :2060-2100
[3]   Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].
Francke, Robert ;
Little, R. Daniel .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521
[4]   Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis [J].
He, Fu-Sheng ;
Ye, Shengqing ;
Wu, Jie .
ACS CATALYSIS, 2019, 9 (10) :8943-8960
[5]   From Molecules to Molecular Surfaces. Exploiting the Interplay Between Organic Synthesis and Electrochemistry [J].
Jing, Qiwei ;
Moeller, Kevin D. .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (01) :135-143
[6]   Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals [J].
Klauck, Felix J. R. ;
James, Michael J. ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (40) :12336-12339
[7]   Kolbe carbon-carbon coupling electrosynthesis using solid-supported bases [J].
Kurihara, Hitoshi ;
Fuchigami, Toshio ;
Tajima, Toshiki .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6888-6890
[8]   Electrophotocatalytic Decarboxylative C-H Functionalization of Heteroarenes [J].
Lai, Xiao-Li ;
Shu, Xiao-Min ;
Song, Jinshuai ;
Xu, Hai-Chao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (26) :10626-10632
[9]   Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators [J].
Lennox, Alastair J. J. ;
Nutting, Jordan E. ;
Stahl, Shannon S. .
CHEMICAL SCIENCE, 2018, 9 (02) :356-361
[10]   Catalyst-free electrochemical decarboxylative cross-coupling of N-hydroxyphthalimide esters and N-heteroarenes towards C(sp3)-C(sp2) bond formation [J].
Liu, Yichang ;
Xue, Liwei ;
Shi, Biyin ;
Bu, Faxiang ;
Wang, Dan ;
Lu, Lijun ;
Shi, Renyi ;
Lei, Aiwen .
CHEMICAL COMMUNICATIONS, 2019, 55 (99) :14922-14925