Visible-light-induced intramolecular sp3 C-H oxidation of 2-alkyl-substituted benzamides for the synthesis of functionalized iminoisobenzofurans

被引：14
|
作者：
Wu, Lingang [1 ]
Hao, Yanan [1 ]
Liu, Yuxiu [1 ]
Wang, Qingmin [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 92期
基金：
中国国家自然科学基金;
关键词：
BOND-DISSOCIATION ENERGIES; PHOTOREDOX CATALYSIS; ASYMMETRIC ALKYLATION; ELECTRON-TRANSFER; RADICALS; AMINATION; ISOBENZOFURAN; CYCLIZATION; AMIDYL;
D O I：
10.1039/c9cc07791j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have developed a protocol for the synthesis of functionalized iminoisobenzofurans by means of visible-light-induced intramolecular cyclization reactions of 2-alkyl-substituted benzamides. This one step-economical protocol, which involves intramolecular sp(3) C-O bond formation, features mild reaction conditions, exclusive chemoselectivity, and high yields.
引用
收藏
页码：13908 / 13911
页数：4
相关论文
共 50 条
  • [41] Visible-light-induced indole synthesis via intramolecular C-N bond formation: desulfonylative C(sp2)-H functionalization
    Li, Quanzhe
    Gu, Xintao
    Wei, Yin
    Shi, Min
    CHEMICAL SCIENCE, 2022, 13 (39) : 11623 - 11632
  • [42] Intramolecular Dehydrogenative Coupling of sp2 C-H and sp3 C-H Bonds: An Expeditious Route to 2-Oxindoles
    Ghosh, Santanu
    De, Subhadip
    Kakde, Badrinath N.
    Bhunia, Subhajit
    Adhikary, Amit
    Bisai, Alakesh
    ORGANIC LETTERS, 2012, 14 (23) : 5864 - 5867
  • [43] Visible-light-induced synthesis of heteroaryl C-glycosides via decarboxylative C-H glycosylation
    Zhang, Cuimei
    He, Dongqin
    Ma, Zhaohui
    Wang, Mi
    Zhu, Yafei
    Liu, Yan
    Chen, Jian
    Lv, Guanghui
    Wu, Yong
    CHEMICAL COMMUNICATIONS, 2024, 60 (45) : 5860 - 5863
  • [44] Visible-Light-Induced Pyridylation of Remote C(sp3)-H Bonds by Radical Translocation of N-Alkoxypyridinium Salts
    Kim, Inwon
    Park, Bohyun
    Kang, Gyumin
    Kim, Jiyun
    Jung, Hoimin
    Lee, Hyeonyeong
    Baik, Mu-Hyun
    Hong, Sungwoo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (47) : 15517 - 15522
  • [45] Visible-light-induced C(sp3)-H functionalizations of piperidines to 3,3-dichloro-2-hydroxy-piperidines with N-chlorosuccinimide
    Wang, Fang
    Liu, Xiaoli
    Wang, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (27) : 6141 - 6146
  • [46] Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway
    Zhang, Yipin
    Dong, Xunqing
    Wu, Yanan
    Li, Guigen
    Lu, Hongjian
    ORGANIC LETTERS, 2018, 20 (16) : 4838 - 4842
  • [47] Visible-Light-Promoted Conversion of Alkyl Benzyl Ether to Alkyl Ester or Alcohol via O-α-sp3 C-H Cleavage
    Lu, Ping
    Hou, Tianyuan
    Gu, Xiangyong
    Li, Pixu
    ORGANIC LETTERS, 2015, 17 (08) : 1954 - 1957
  • [48] Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 C-H oxidation
    He, Chao
    Zhang, Xiaohui
    Huang, Ruofeng
    Pan, Jing
    Li, Jiaqiang
    Ling, Xuege
    Xiong, Yan
    Zhu, Xiangming
    TETRAHEDRON LETTERS, 2014, 55 (32) : 4458 - 4462
  • [49] Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds
    Chen, Hang
    Zhou, Yang
    Lei, Panpan
    Wang, Haifeng
    Yan, Qiongjiao
    Properzi, Roberta
    Wang, Wei
    Jing, Linhai
    Chen, Fener
    GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (04): : 350 - 354
  • [50] Efficient Photolytic Halogenation and Oxidation of Unactivated Alkyl sp3 C-H Bonds with Iodine(III)
    Jia, Hao
    Li, Nan
    Tang, Chunmei
    Wang, Yajuan
    Xi, Yonghao
    Liao, Rongbao
    Xu, Wei
    Wu, Fufang
    Shen, Xiaobao
    Zhai, Hongbin
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (05) : 505 - 510
12345