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
相关论文
共 87 条
  • [1] s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles
    An, Wan-Kai
    Zheng, Shi-Jia
    Zhang, Hui-Xing
    Shang, Tian-Tian
    Wang, He-Rui
    Xu, Xiao-Jing
    Jin, Qiu
    Qin, Yuchen
    Ren, Yunlai
    Jiang, Song
    Xu, Cui-Lian
    Hou, Mao-Song
    Pan, Zhenliang
    [J]. GREEN CHEMISTRY, 2021, 23 (03) : 1292 - 1299
  • [2] Iron-Catalyzed C-H Alkylation of Heterocyclic C-H Bonds
    Babu, Kaki Raveendra
    Zhu, Nengbo
    Bao, Hongli
    [J]. ORGANIC LETTERS, 2017, 19 (01) : 46 - 49
  • [3] Metal-free direct C-H phosphonation of N-heterocycles with diphenylphosphine oxides under mild conditions
    Cai, Zhao-Nan
    Han, Ya-Ping
    Zhang, Yuecheng
    Zhang, Hong-Yu
    Zhao, Jiquan
    Yang, Shang-Dong
    [J]. GREEN CHEMISTRY, 2023, 25 (14) : 5721 - 5726
  • [4] Chemistry, biological properties and SAR analysis of quinoxalinones
    Carta, A.
    Piras, S.
    Loriga, G.
    Paglietti, G.
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2006, 6 (11) : 1179 - 1200
  • [5] Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in Three-Component Alkyl-Fluorination of Olefins with a Fluoride Ion
    Deng, Weili
    Feng, Weiwei
    Li, Yajun
    Bao, Hongli
    [J]. ORGANIC LETTERS, 2018, 20 (14) : 4245 - 4249
  • [6] High Power- and Energy-Density Supercapacitors through the Chlorine Respiration Mechanism
    Fan, Xiaotong
    Huang, Kai
    Chen, Long
    You, Haipeng
    Yao, Menglei
    Jiang, Hao
    Zhang, Ling
    Lian, Cheng
    Gao, Xiangwen
    Li, Chunzhong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (02)
  • [7] Sustainable valorisation of renewables through dialkyl carbonates and isopropenyl esters
    Fiorani, Giulia
    Perosa, Alvise
    Selva, Maurizio
    [J]. GREEN CHEMISTRY, 2023, 25 (13) : 4878 - 4911
  • [8] Metal-and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
    Gan, Shaoyan
    Yin, Junjie
    Yao, Yuan
    Liu, Yang
    Chang, Denghu
    Zhu, Dan
    Shi, Lei
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (12) : 2647 - 2654
  • [9] Visible-Light-Induced Phosphorylation of Imidazo-Fused Heterocycles under Metal-Free Conditions
    Gao, Fan
    Sun, Kai
    Chen, Xiao-Lan
    Shi, Tao
    Li, Xiao-Yun
    Qu, Ling-Bo
    Zhao, Yu-Fen
    Yu, Bing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (22) : 14744 - 14752
  • [10] Alkyl Esterification of Vinylarenes Enabled by Visible-Light-Induced Decarboxylation
    Ge, Liang
    Li, Yajun
    Jian, Wujun
    Bao, Hongli
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (49) : 11767 - 11770