Tertiary-Alcohol-Directed Functionalization of Remote C(sp3)-H Bonds by Sequential Hydrogen Atom and Heteroaryl Migrations

被引：178
|
作者：
Wu, Xinxin [1 ]
Wang, Mingyang [1 ]
Huan, Leitao [1 ]
Wang, Dongping [1 ]
Wang, Jinwei [1 ]
Zhu, Chen [1 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 06期
基金：
中国国家自然科学基金;
关键词：
C-H activation; electron transfer; heteroaryls; photocatalysis; radicals; VISIBLE-LIGHT PHOTOCATALYSIS; COUPLED ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; ALKOXY RADICALS; PHOTOCHEMICAL-REACTION; H BONDS; GENERATION; CLEAVAGE; TETRAHYDROFURANS; HYPOCHLORITES;
D O I：
10.1002/anie.201709025
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reported for the first time is a tertiary-alcohol-guided heteroarylation of remote C(sp(3))-H bonds. The mild and direct generation of alkoxyl radicals from alcohols is enabled by visible-light photocatalysis. A remote hydrogen atom and heteroaryl migration sequence are involved in the reaction. Many sensitive groups remain intact in the reaction, thus illustrating wide functional-group compatibility. This protocol provides a practical strategy for the late-stage modification of alkyl ketones.
引用
收藏
页码：1640 / 1644
页数：5
相关论文
共 50 条
  • [21] Gold(I)-Catalyzed Functionalization of Benzhydryl C(sp3)-H Bonds
    Cera, Gianpiero
    Chiarucci, Michel
    Dosi, Federico
    Bandini, Marco
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2227 - 2231
  • [22] Palladium(II)-Catalyzed Enantioselective Functionalization of C(sp3)-H Bonds
    Han Yeqiang
    Shi Bingfeng
    ACTA CHIMICA SINICA, 2023, 81 (11) : 1522 - 1540
  • [23] Polymerization-Enhanced Photocatalysis for the Functionalization of C(sp3)-H Bonds
    Zhu, Shan-Shan
    Liu, Yan
    Chen, Xiao-Lan
    Qu, Ling-Bo
    Yu, Bing
    ACS CATALYSIS, 2022, 12 (01) : 126 - 134
  • [24] Functionalization of C(sp3)-H bonds using a transient directing group
    Zhang, Fang-Lin
    Hong, Kai
    Li, Tuan-Jie
    Park, Hojoon
    Yu, Jin-Quan
    SCIENCE, 2016, 351 (6270) : 252 - 256
  • [25] Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)-H Bonds
    Ma, Dengke
    Zhang, Zhihan
    Chen, Min
    Lin, Zhenyang
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (44) : 15916 - 15921
  • [26] 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
  • [27] γ,δ,ε-C(sp3)-H Functionalization through Directed Radical H-Abstraction
    Liu, Tao
    Mei, Tian-Sheng
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) : 5871 - 5874
  • [28] Brønsted acid-enhanced direct hydrogen atom transfer photocatalysis for selective functionalization of unactivated C(sp3)-H bonds
    Cao, Hui
    Kong, Degong
    Yang, Li-Cheng
    Chanmungkalakul, Supphachok
    Liu, Tao
    Piper, Jared L.
    Peng, Zhihui
    Gao, Linlin
    Liu, Xiaogang
    Hong, Xin
    Wu, Jie
    NATURE SYNTHESIS, 2022, 1 (10): : 794 - 803
  • [29] N-Heterocyclic Carbene Enabled Functionalization of Inert C(Sp3)-H Bonds via Hydrogen Atom Transfer (HAT) Processes
    Lu, Fengfei
    Su, Fen
    Pan, Shijie
    Wu, Xiuli
    Wu, Xingxing
    Chi, Yonggui Robin
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (47)
  • [30] Brønsted acid-enhanced direct hydrogen atom transfer photocatalysis for selective functionalization of unactivated C(sp3)–H bonds
    Hui Cao
    Degong Kong
    Li-Cheng Yang
    Supphachok Chanmungkalakul
    Tao Liu
    Jared L. Piper
    Zhihui Peng
    Linlin Gao
    Xiaogang Liu
    Xin Hong
    Jie Wu
    Nature Synthesis, 2022, 1 : 794 - 803
12345