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

被引：17
|
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
  • [1] Copper-Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones
    Dos Santos, Aurelie
    El Kaim, Laurent
    Grimaud, Laurence
    Ronsseray, Caroline
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (17) : 3117 - 3121
  • [2] Copper-catalyzed C-C bond cleavage and intramolecular cyclization: an approach toward acridones
    Zhou, Wang
    Yang, Youqing
    Liu, Yong
    Deng, Guo-Jun
    GREEN CHEMISTRY, 2013, 15 (01) : 76 - 80
  • [3] Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage of Unstrained Ketones with Air and Amines
    Zhou, Wang
    Fan, Wenyou
    Jiang, Qijian
    Lang, Yu-Feng
    Jiao, Ning
    ORGANIC LETTERS, 2015, 17 (10) : 2542 - 2545
  • [4] Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides
    Yang, Guo-Ping
    Li, Ke
    Liu, Wei
    Zeng, Kai
    Liu, Yu-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (35) : 6958 - 6964
  • [5] Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
    Tnay, Ya Lin
    Ang, Gim Yean
    Chiba, Shunsuke
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1933 - 1943
  • [6] Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
    Fan, Wenyou
    Yang, Youqing
    Lei, Jianhua
    Jiang, Qijian
    Zhou, Wang
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8782 - 8789
  • [7] Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage for C-N Bond Formation: From Ketones to Amides
    Tang, Conghui
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6528 - 6532
  • [8] Copper-catalyzed oxidative amidation of α,β-unsaturated ketones via selective C-H or C-C bond cleavage
    Pouambeka, Tony Wheellyam
    Zhang, Ge
    Zheng, Guang-Fan
    Xu, Guo-Xing
    Zhang, Qian
    Xiong, Tao
    Zhang, Qian
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1420 - 1424
  • [9] Copper-Catalyzed Aerobic 6-Endo-Trig Cyclization of β,γ-Unsaturated Hydrazones for the Divergent Synthesis of Dihydropyridazines and Pyridazines
    Fan, Zhenwei
    Pan, Zhangjin
    Huang, Liangsen
    Cheng, Jiajia
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 4236 - 4245
  • [10] Copper-catalyzed enantioselective diyne cyclization via C(sp2)-O bond cleavage
    Zhou, Ji-Jia
    Meng, Ya-Nan
    Liu, Li-Gao
    Liu, Yi-Xi
    Xu, Zhou
    Lu, Xin
    Zhou, Bo
    Ye, Long-Wu
    CHEMICAL SCIENCE, 2023, 14 (13) : 3493 - 3500
12345