Copper-Catalyzed Aerobic Cyclization of ß,γ-Unsaturated Hydrazones with Concomitant C=C Bond Cleavage

被引：19
|
作者：
Fan, Zhenwei [1 ]
Feng, Jiahao [1 ]
Hou, Yuchen [1 ]
Rao, Min [1 ]
Cheng, Jiajia [1 ]
机构：
[1] Fuzhou Univ, Key Lab Mol Synth & Funct Discovery, Coll Chem,Fujian Prov Univ, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 20期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; C-H AMINATION; OXIDATIVE CLEAVAGE; LIGHT; PYRAZOLES; RADICALS; HYDROAMINATION; OLEFINS; OXYGEN;
D O I：
10.1021/acs.orglett.0c02911
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu-catalyzed aerobic oxidative cyclization of ss,gamma-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant C=C bond cleavage of ss,gamma-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.
引用
收藏
页码：7981 / 7985
页数：5
相关论文
共 50 条
  • [31] Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
    Rostami, Abed
    Rostami, Amin
    Ghaderi, Arash
    Gholinejad, Mohammad
    Gheisarzadeh, Sajedeh
    SYNTHESIS-STUTTGART, 2017, 49 (22): : 5025 - 5038
  • [32] TEMPO-catalyzed Aerobic Oxygenation and Nitrogenation of Olefins via C=C Double-Bond Cleavage
    Wang, Teng
    Jiao, Ning
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 11692 - 11695
  • [33] Copper-Catalyzed Aerobic Aliphatic C-H Oxygenation Directed by an Amidine Moiety
    Wang, Yi-Feng
    Chen, Hui
    Zhu, Xu
    Chiba, Shunsuke
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 11980 - 11983
  • [34] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [35] Cu-Catalyzed aerobic oxidative cleavage of C(sp3)-C(sp3) bond: Synthesis of α-ketoamides
    Zhang, Jingming
    Liu, Chengkou
    Yang, Man
    Fang, Zheng
    Guo, Kai
    TETRAHEDRON LETTERS, 2020, 61 (47)
  • [36] Eosin Y catalyzed visible light mediated aerobic photo-oxidative cleavage of the C-C double bond of styrenes
    Singh, Atul K.
    Chawla, Ruchi
    Yadav, La Dhar S.
    TETRAHEDRON LETTERS, 2015, 56 (05) : 653 - 656
  • [37] Efficient synthetic route to bisaryl ketones via copper-catalyzed C-C triple bonds cleavage
    Li, Xiangguang
    Huang, Wenzhong
    Liang, Deqiang
    Yuan, Lin
    Ma, Yinhai
    Gu, Lijun
    TETRAHEDRON, 2015, 71 (07) : 1045 - 1049
  • [38] Aerobic Copper-Catalyzed Organic Reactions
    Allen, Scott E.
    Walvoord, Ryan R.
    Padilla-Salinas, Rosaura
    Kozlowski, Marisa C.
    CHEMICAL REVIEWS, 2013, 113 (08) : 6234 - 6458
  • [39] Copper-catalyzed oxidative amidation of dibenzylamines via C-H bond activation
    Hu, Jinjin
    Zuo, Xiujin
    Huang, Hanmin
    CHINESE JOURNAL OF CATALYSIS, 2013, 34 (09) : 1644 - 1650
  • [40] Copper-Catalyzed Electrophilic Amination: An Umpolung Strategy for New C -N Bond Formations
    Hirano, Koji
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2023, 96 (03) : 198 - 207
12345