Nickel-Catalyzed Stereoselective Dicarbofunctionalization of Alkynes

被引:103
|
作者
Li, Zhaodong [1 ]
Garcia-Dominguez, Andres [1 ]
Nevado, Cristina [1 ]
机构
[1] Univ Zurich, Dept Chem, Winterthurerstr 190, CH-8057 Zurich, Switzerland
基金
欧洲研究理事会; 瑞士国家科学基金会;
关键词
alkyl halides; alkynes; boron; nickel; radicals; TETRASUBSTITUTED ALKENES; TERMINAL ALKYNES; GRIGNARD-REAGENTS; RADICAL REACTIONS; ARYL HALIDES; IODIDES; IRON; ELECTROPHILES; CARBOZINCATION; 1,2-ADDITION;
D O I
10.1002/anie.201601296
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anickel-catalyzed three-component reaction involving terminal alkynes, boronic acids, and alkyl halides is presented herein. Trisubstituted alkenes can be obtained in a highly regio- and stereocontrolled manner by the simultaneous addition of both aryl and alkyl groups across the triple bond in a radical-mediated process. The reaction, devoid of air- and moisture-sensitive organometallic reagents and catalysts, is operationally simple and offers a broad scope and functional-group tolerance.
引用
收藏
页码:6938 / 6941
页数:4
相关论文
共 50 条
  • [41] Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization
    Campbell, Mark W.
    Yuan, Mingbin
    Polites, Viktor C.
    Gutierrez, Osvaldo
    Molander, Gary A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (10) : 3901 - 3910
  • [42] Stereoselective synthesis of fluoroalkylated (Z)-alkene via nickel-catalyzed and iron-mediated hydrofluoroalkylation of alkynes
    Li, Xiang-Rui
    Li, Wen-Xin
    Zhang, Zhuo-Wen
    Shen, Chuanji
    Zhou, Xiaocong
    Chu, Xue-Qiang
    Rao, Weidong
    Shen, Zhi-Liang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22) : 6377 - 6383
  • [43] Nickel-catalyzed carbostannylation of alkynes with allyl-, acyl-, and alkynylstannanes: Stereoselective synthesis of trisubstituted vinylstannanes
    Shirakawa, E
    Yamasaki, K
    Yoshida, H
    Hiyama, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) : 10221 - 10222
  • [44] Cobalt- and Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling of Alkynes, Allenes, and Alkenes with Alkenes
    Jeganmohan, Masilamani
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) : 10876 - 10886
  • [45] Nickel-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Alkynes with Formic Acid through Catalytic CO Recycling
    Fu, Ming-Chen
    Shang, Rui
    Cheng, Wan-Min
    Fu, Yao
    ACS CATALYSIS, 2016, 6 (04): : 2501 - 2505
  • [46] Enantioselective Nickel-Catalyzed Reductive Coupling of Alkynes and Imines
    Zhou, Chang-Yue
    Zhu, Shou-Fei
    Wang, Li-Xin
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) : 10955 - 10957
  • [47] Palladium- and nickel-catalyzed intramolecular cyanoboration of alkynes
    Suginome, M
    Yamamoto, A
    Murakami, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6358 - 6359
  • [48] Mechanistic Investigation of the Nickel-Catalyzed Transfer Hydrocyanation of Alkynes
    Reisenbauer, Julia C.
    Finkelstein, Patrick
    Ebert, Marc-Olivier
    Morandi, Bill
    ACS CATALYSIS, 2023, 13 (17) : 11548 - 11555
  • [49] Nickel-Catalyzed Tetramerization of Alkynes: Synthesis and Structure of Octatetraenes
    Wu, Tsun-Cheng
    Chen, Jheng-Jhih
    Wu, Yao-Ting
    ORGANIC LETTERS, 2011, 13 (18) : 4794 - 4797
  • [50] Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides
    Hua, Ruimao
    Takeda, Hideaki
    Onozawa, Shun-ya
    Abe, Yoshimoto
    Tanaka, Masato
    ORGANIC LETTERS, 2007, 9 (02) : 263 - 266