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

被引:43
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
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共 87 条
  • [21] Iron-Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source
    Jian, Wujun
    Ge, Liang
    Jiao, Yihang
    Qian, Bo
    Bao, Hongli
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) : 3650 - 3654
  • [22] Visible-Light Photoredox Decarboxylative Couplings
    Jin, Yunhe
    Fu, Hua
    [J]. 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
    Kawamura, Shintaro
    Mukherjee, Subrata
    Sodeoka, Mikiko
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (10) : 2096 - 2109
  • [24] Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry
    Kong, Xianqiang
    Chen, Yiyi
    Liu, Qianwen
    Wang, WenJie
    Zhang, Shuangquan
    Zhang, Qian
    Chen, Xiaohui
    Xu, Yuan-Qing
    Cao, Zhong-Yan
    [J]. ORGANIC LETTERS, 2023, 25 (04) : 581 - 586
  • [25] Visible Light Driving Alkene Difunctionalization Reaction Involving Group Migration
    Li Meng
    Zhao Dongyang
    Sun Kai
    [J]. 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
    Li, Ningbo
    Wang, Yuxin
    Gu, Shuo
    Hu, Chuqian
    Yang, Qian
    Jin, Zhaohui
    Ouyang, Wen-Tao
    Qiao, Jie
    He, Wei-Min
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (02) : 370 - 374
  • [27] Visible Light-Promoted Radical Reactions of Diazo Compounds
    Li Sen
    Zhou Lei
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 3944 - 3958
  • [28] Recent Progress on Radical Decarboxylative Alkylation for Csp3-C Bond Formation
    Li, Yajun
    Ge, Liang
    Muhammad, Munira Taj
    Bao, Hongli
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (24): : 5263 - 5284
  • [29] Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides
    Li, Yougui
    Ge, Liang
    Qian, Bo
    Babu, Kaki Raveendra
    Bao, Hongli
    [J]. TETRAHEDRON LETTERS, 2016, 57 (50) : 5677 - 5680
  • [30] Photocatalytic chemo-, regio- & stereoselective olefinic β-C-H decarboxylative alkylation of enamides with diacyl peroxides
    Liu, Han
    Wu, Yechun
    Liu, Lingli
    Yu, Jin-Tao
    Pan, Changduo
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (55) : 8556 - 8559