The functionalization of a cascade of C(sp2)-H/C(sp3)-H bonds: synthesis of fused dihydropyrazoles via visible-light photoredox catalysis

被引：38
|
作者：
Cheng, Jian [1 ]
Xu, Pan [1 ]
Li, Weipeng [1 ]
Cheng, Yixiang [1 ]
Zhu, Chengjian [1 ,2 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210023, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 80期
基金：
中国国家自然科学基金;
关键词：
PHOTOCATALYTIC GENERATION; DUAL CATALYSIS; STRATEGY; DIFLUOROALKYLATION; CYCLIZATION; DISCOVERY; ARYLATION; RADICALS; AMINES;
D O I：
10.1039/c6cc06410h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The functionalization of a cascade of C(sp(2))-H/C(sp(3))-H bonds in aldehyde hydrazones with simple 2,2-dibromo-1,3-dicarbonyls was achieved via visible-light photoredox catalysis. This method, which involves free radical addition, polar crossover and 6 pi electrocyclic reaction, provides an efficient approach for the synthesis of complex fused dihydropyrazoles and related derivatives with moderate to good yields and excellent regioselectivity under mild reaction conditions.
引用
收藏
页码：11901 / 11904
页数：4
相关论文
共 50 条
  • [1] Regioselective functionalization of sp2 and sp3 C-H bonds
    Daugulis, Olafs
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [2] Functionalization of sp2 and sp3 C-H bonds via deprotonative zincation
    Wang, Qiu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [3] C(sp3)-H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis
    Wakaki, Takayuki
    Sakai, Kentaro
    Enomoto, Takafumi
    Kondo, Mio
    Masaoka, Shigeyuki
    Oisaki, Kounosuke
    Kanai, Motomu
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (32) : 8051 - 8055
  • [4] Alkylarylation of styrenes via direct C(sp3)-Br/C(sp2)-H functionalization mediated by photoredox and copper cooperative catalysis
    Yong, Xin
    Han, Ya-Fei
    Li, Yang
    Song, Ren-Jie
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2018, 54 (91) : 12816 - 12819
  • [5] Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Mondal, Pradip Kumar
    CHEMICAL COMMUNICATIONS, 2019, 55 (65) : 9689 - 9692
  • [6] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
    Wei, Wan-Xu
    Czajkowski, Mateusz
    Kuang, Yangjin
    Nguyen, Tu-Anh V.
    Qin, Bo
    Tomanik, Martin
    ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546
  • [7] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups
    Rouquet, Guy
    Chatani, Naoto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11726 - 11743
  • [8] Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp3)-H/C(sp3)-H and C(sp3)-H/C(sp2)-H via Intermolecular HAT
    Xie, Xinpeng
    Qiao, Kaikai
    Shao, Bing-ru
    Jiang, Wenfeng
    Shi, Lei
    ORGANIC LETTERS, 2023, 25 (23) : 4264 - 4269
  • [9] Revealing Silylation of C(sp2)/C(sp3)-H Bonds in Arylphosphines by Ruthenium Catalysis
    Wen, Jian
    Dong, Ben
    Zhu, Jinjun
    Zhao, Yue
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (27) : 10909 - 10912
  • [10] Revealing Silylation of C(sp2)/C(sp3)-H Bonds in Arylphosphines by Ruthenium Catalysis
    Zheng, Guangfan
    Li, Xingwei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2994 - 2996
12345