Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

被引:57
作者
Cheng, Fukun [1 ,2 ]
Fan, Lulu [2 ]
Lv, Qiyan [1 ,3 ]
Chen, Xiaolan [1 ]
Yu, Bing [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[2] Henan Univ Technol, Coll Chem & Chem Engn, Zhengzhou 450001, Peoples R China
[3] Nanjing Forestry Univ, Natl Engn Res Ctr Low Carbon Proc & Utilizat Fore, Nanjing 210037, Peoples R China
基金
中国国家自然科学基金;
关键词
ARYL ACYL PEROXIDES; C-H ALKYLATION; PHOTOREDOX CATALYSIS; UNACTIVATED ALKENES; ADDITIVE-FREE; EFFICIENT; QUINOXALIN-2(1H)-ONES; VINYLARENES; ARYLATION; HALIDES;
D O I
10.1039/d3gc02545d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C-H alkylation of N-heteroaromatics. With this metal-/base-/additive-free photocatalytic system, 57 examples of alkylated N-heteroaromatics scaffolds including 1,2,4-triazine-3,5(2H,4H)-diones (i.e. azauracils), quinoxalin-2(1H)-ones, 2H-benzo[b][1,4]oxazin-2-ones and quinoxalines were successfully synthesized.
引用
收藏
页码:7971 / 7977
页数:7
相关论文
共 87 条
[21]   Iron-Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source [J].
Jian, Wujun ;
Ge, Liang ;
Jiao, Yihang ;
Qian, Bo ;
Bao, Hongli .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) :3650-3654
[22]   Visible-Light Photoredox Decarboxylative Couplings [J].
Jin, Yunhe ;
Fu, Hua .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) :368-385
[23]   Recent advances in reactions using diacyl peroxides as sources of O- and C-functional groups [J].
Kawamura, Shintaro ;
Mukherjee, Subrata ;
Sodeoka, Mikiko .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (10) :2096-2109
[24]   Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry [J].
Kong, Xianqiang ;
Chen, Yiyi ;
Liu, Qianwen ;
Wang, WenJie ;
Zhang, Shuangquan ;
Zhang, Qian ;
Chen, Xiaohui ;
Xu, Yuan-Qing ;
Cao, Zhong-Yan .
ORGANIC LETTERS, 2023, 25 (04) :581-586
[25]   Visible Light Driving Alkene Difunctionalization Reaction Involving Group Migration [J].
Li Meng ;
Zhao Dongyang ;
Sun Kai .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) :4152-4168
[26]   Visible-light-initiated external photocatalyst-free synthesis of α,α-difluoro-β-ketoamides from 4-aminocoumarins [J].
Li, Ningbo ;
Wang, Yuxin ;
Gu, Shuo ;
Hu, Chuqian ;
Yang, Qian ;
Jin, Zhaohui ;
Ouyang, Wen-Tao ;
Qiao, Jie ;
He, Wei-Min .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (02) :370-374
[27]   Visible Light-Promoted Radical Reactions of Diazo Compounds [J].
Li Sen ;
Zhou Lei .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) :3944-3958
[28]   Recent Progress on Radical Decarboxylative Alkylation for Csp3-C Bond Formation [J].
Li, Yajun ;
Ge, Liang ;
Muhammad, Munira Taj ;
Bao, Hongli .
SYNTHESIS-STUTTGART, 2017, 49 (24) :5263-5284
[29]   Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides [J].
Li, Yougui ;
Ge, Liang ;
Qian, Bo ;
Babu, Kaki Raveendra ;
Bao, Hongli .
TETRAHEDRON LETTERS, 2016, 57 (50) :5677-5680
[30]   Photocatalytic chemo-, regio- & stereoselective olefinic β-C-H decarboxylative alkylation of enamides with diacyl peroxides [J].
Liu, Han ;
Wu, Yechun ;
Liu, Lingli ;
Yu, Jin-Tao ;
Pan, Changduo .
CHEMICAL COMMUNICATIONS, 2023, 59 (55) :8556-8559