Highly efficient copper-catalyzed nitro-mannich type reaction:: Cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond

被引:516
|
作者
Li, ZP [1 ]
Li, CJ [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ja050058j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel C-C bond formation method was developed via the cross-dehydrogenative-coupling (CDC) reaction catalyzed by using copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct β-nitroamine via the reaction between sp3 C-H and sp3 C-H bonds. Copyright © 2005 American Chemical Society.
引用
收藏
页码:3672 / 3673
页数:2
相关论文
共 50 条
  • [31] Copper-catalyzed SP3 C-H etherification via acyl protected phenols
    Salvador, Tolani
    Arnett-Guardado, Carlos
    Sapiezynski, Nicholas
    Warren, Timothy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [32] 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
  • [33] C(sp3)-H/C(sp3)-H Dehydrogenative Radical Coupling of Glycine Derivatives
    Wang, Jiayuan
    Ye, Youwan
    Sang, Tongzhi
    Zhou, Chenxing
    Bao, Xiazhen
    Yuan, Yong
    Huo, Congde
    ORGANIC LETTERS, 2022, 24 (41) : 7577 - 7582
  • [34] A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C-H Bond Activation Followed by C-C and C-O Bond Formation
    Gogoi, Anupal
    Guin, Srimanta
    Rout, Saroj Kumar
    Patel, Bhisma K.
    ORGANIC LETTERS, 2013, 15 (08) : 1802 - 1805
  • [35] 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
  • [36] Copper-Catalyzed Benzylic sp3 C-H Amination Reaction of Amidines : Synthesis of Quinazoline Derivatives
    Zhang Qian
    Lu Yunhe
    Li Yan
    Xiong Tao
    Zhang Qian
    ACTA CHIMICA SINICA, 2014, 72 (11) : 1139 - 1143
  • [37] Construction of C-O bond via cross-dehydrogenative coupling of sp [3] C-H bond with phenols catalyzed by copper porphyrin
    Yang, Shuang
    Xiong, Ming-Feng
    Tian, Wan-Qun
    Zhang, Hao
    Xiao, Xin-Yan
    Liu, Hai-Yang
    Chang, Chi-Kwong
    TETRAHEDRON, 2020, 76 (45)
  • [38] Merging Photoredox with Bronsted Acid Catalysis: The Cross-Dehydrogenative C-O Coupling for sp3 C-H Bond Peroxidation
    Xia, Qing
    Wang, Qiang
    Yan, Changcun
    Dong, Jianyang
    Song, Hongjian
    Li, Ling
    Liu, Yuxiu
    Wang, Qingmin
    Liu, Xiangming
    Song, Haibin
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (45) : 10871 - 10877
  • [39] A Catalytic Alkylation of Ketones via sp3 C-H Bond Activation
    Peng, Xue
    Hirao, Yuki
    Yabu, Shunsuke
    Sato, Hirofumi
    Higashi, Masahiro
    Akai, Takuya
    Masaoka, Shigeyuki
    Mitsunuma, Harunobu
    Kanai, Motomu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6333 - 6346
  • [40] Cationic Ir(I)-Catalyzed sp3 C-H Bond Alkenylation of Amides with Alkynes
    Tsuchikama, Kyoji
    Kasagawa, Mitsugu
    Endo, Kohei
    Shibata, Takanori
    ORGANIC LETTERS, 2009, 11 (08) : 1821 - 1823