Copper-Catalyzed C(sp3)-Amination of Ketone-Derived Dihydroquinazolinones by Aromatization-Driven C-C Bond Scission

被引：38
|
作者：
Lv, Xin-Yang [1 ,2 ]
Abrams, Roman [1 ]
Martin, Ruben [1 ,3 ]
机构：
[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain
[2] Univ Rovira i Virgili, Dept Quim Analit & Quim Organ, C-Marcel li Domingo, 1, Tarragona 43007, Spain
[3] Passeig Lluis Co, Catalan Inst Res & Adv Studies ICREA, 23, Barcelona 08010, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 08期
基金：
欧洲研究理事会;
关键词：
Amination; C-C Functionalization; Copper; Ketones; Proaromaticity; SECONDARY ALKYL-HALIDES; CARBON-CARBON BONDS; ACTIVATION; AMINES; AMIDATION; IMIDATION; COUPLINGS; OXIDATION;
D O I：
10.1002/anie.202217386
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we describe the development of a copper-catalyzed C(sp(3))-amination of proaromatic dihydroquinazolinones derived from ketones. The reaction is enabled by the intermediacy of open-shell species arising from homolytic C-C bond-cleavage driven by aromatization. The protocol is characterized by its operational simplicity and generality, including chemical diversification of advanced intermediates.
引用
收藏
页数：6
相关论文
共 50 条
  • [1] Organo-photoredox catalyzed gem-difluoroallylation of ketone-derived dihydroquinazolinones via C(sp3)-C bond and C(sp3)-F bond cleavage
    Zhang, Yue
    Zhu, Tianshuai
    Lin, Yuqian
    Wei, Xian
    Xie, Xinyu
    Lin, Ruofan
    Zhang, Zhijie
    Fang, Weiwei
    Zhang, Jing-Jing
    Zhang, Yue
    Hu, Meng-Yang
    Cai, Lingchao
    Chen, Zhen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (27) : 5561 - 5568
  • [2] Copper-Catalyzed Aromatization-Driven Ring-Opening Amination and Oxygenation of Spiro Dihydroquinazolinones
    Li, Wenke
    Miao, Hong-Jie
    Zhang, Jin-Hua
    Duan, Xin-Hua
    Guo, Li-Na
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (58)
  • [3] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
  • [4] Copper-Catalyzed Cyanoalkylation of Amines via C-C Bond Cleavage: An Approach for C(sp3)-N Bond Formations
    Yang, Lin
    Zhang, Jia-Yu
    Duan, Xin-Hua
    Gao, Pin
    Jiao, Jiao
    Guo, Li-Na
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (13): : 8615 - 8629
  • [5] Copper-Catalyzed Remote C(sp3)-H Amination of Carboxamides
    Min, Qing-Qang
    Yang, Jia-Wen
    Pang, Meng Juan
    Ao, Gui-Zhen
    Liu, Feng
    ORGANIC LETTERS, 2020, 22 (07) : 2828 - 2832
  • [6] Copper-catalyzed amination of an -C(sp3)-H bond in inactivated ethers to synthesize α-aminonitriles
    Yuan, Zaifeng
    Zhu, Chunyu
    Ma, Zhixian
    Xia, Chengfeng
    CHEMICAL COMMUNICATIONS, 2018, 54 (78) : 11033 - 11036
  • [7] Copper-catalyzed transfer methylenation via C(sp3)-C(sp3) bond cleavage of alcohols
    Hong, Chuan-Ming
    Zhuang, Xin
    Luo, Zhen
    Xiong, Si-Qi
    Liu, Zheng-Qiang
    Li, Qing-Lin
    Zou, Fei-Fei
    Li, Qing-Hua
    Liu, Tang-Lin
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6547 - 6555
  • [8] Ketone-derived 2,3-dihydroquinazolinones in N-heteroarene C-H alkylation via C-C bond scission under oxidative metal catalysis
    Mondal, Pinku Prasad
    Pal, Amit
    Prakash, Athira K.
    Sahoo, Basudev
    CHEMICAL COMMUNICATIONS, 2022, 58 (95) : 13202 - 13205
  • [9] Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles
    Jin, Ruo-Xing
    Dai, Jing-Cheng
    Li, Yan
    Wang, Xi-Sheng
    ORGANIC LETTERS, 2021, 23 (02) : 421 - 426
  • [10] Unexpected Copper-Catalyzed Aerobic Oxidative Cleavage of C(sp3)-C(sp3) Bond of Glycol Ethers
    Liu, Zhong-Quan
    Zhao, Lixing
    Shang, Xiaojie
    Cui, Zili
    ORGANIC LETTERS, 2012, 14 (12) : 3218 - 3221
12345