Copper(II)-Mediated Dehydrogenative Cross-Coupling of Heteroarenes

被引:90
|
作者
Mao, Zhifeng [1 ]
Wang, Zhe [2 ]
Xu, Zhaoqing [1 ,2 ]
Huang, Fei [1 ]
Yu, Zhengkun [1 ]
Wang, Rui [2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
关键词
C-H BONDS; COPPER-CATALYZED ARYLATION; GENERAL-METHOD; ARYL BROMIDES; SOLE OXIDANT; PALLADIUM; AZOLES; FUNCTIONALIZATIONS; HETEROCYCLES; ACIDS;
D O I
10.1021/ol301517y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cu(OAc)(2)-mediated dehydrogenative cross-coupling between two heteroarenes has been realized in the absence of any other additive. A mechanism involving a formal Cu(II) to Cu(0) route by convergent disproportionation of the copper mediator is proposed and has been evidenced by copper mirror formation during the reaction. This synthetic protocol provides a concise and "green" access to unsymmetrical biheteroarenes bearing structural motifs of substantial utility in organic synthesis.
引用
收藏
页码:3854 / 3857
页数:4
相关论文
共 50 条
  • [41] Illuminating aryl cross-coupling with copper
    Li, Haoyu
    Chiba, Shunsuke
    NATURE SYNTHESIS, 2022, 1 (05): : 339 - 340
  • [42] Catalytic cross-coupling with copper and light
    Peters, Jonas C.
    Fu, Gregory
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [43] Illuminating aryl cross-coupling with copper
    Haoyu Li
    Shunsuke Chiba
    Nature Synthesis, 2022, 1 : 339 - 340
  • [44] Cross-coupling of copper alkynides with allyl
    Kurts, AL
    Matveeva, ED
    Erin, AS
    Kvasha, MP
    VESTNIK MOSKOVSKOGO UNIVERSITETA SERIYA 2 KHIMIYA, 1996, 37 (02): : 151 - 155
  • [45] Diastereoselective Formation of Cyclopropanols by a Chromium(II)-mediated Cross-coupling Reaction
    Lang, Steffen
    Groth, Ulrich
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (08): : 980 - 984
  • [46] Copper(II) Acetate-Mediated Cross-Coupling of Phenylboronic Acids with Aryloximes: Synthesis of O-Aryloximes
    Feng, Xing-Hua
    Zhang, Guo-Zhen
    Chen, Cheng-Qun
    Yang, Ming-Yu
    Xu, Xiao-Yun
    Huang, Guo-Sheng
    SYNTHETIC COMMUNICATIONS, 2009, 39 (10) : 1768 - 1780
  • [47] Copper-Mediated Cross-Dehydrogenative Coupling Reaction of Pyrrole and Indole Derivatives with Thiols
    Ma, Wenbo
    Xu, Yue
    Gu, Qilin
    Zheng, Tao
    Gu, Linghui
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (08)
  • [48] Ascorbate mediated copper catalyzed reductive cross-coupling of disulfides with aryl iodides
    Martinek, Marek
    Korf, Michal
    Srogl, Jiri
    CHEMICAL COMMUNICATIONS, 2010, 46 (24) : 4387 - 4389
  • [49] Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols
    Herradura, PS
    Pendola, KA
    Guy, RK
    ORGANIC LETTERS, 2000, 2 (14) : 2019 - 2022
  • [50] Electrochemical synthesis of symmetrical benzidines through dehydrogenative cross-coupling reaction
    Liu, Xiaoying
    Cai, Tian-Cheng
    Guo, Dingyi
    Wang, Bin-Bin
    Ying, Shengneng
    Wang, Huixian
    Tang, Shiyun
    Shen, Qinpeng
    Gui, Qing-Wen
    TETRAHEDRON LETTERS, 2021, 70