Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes

被引：35
|
作者：
Wei, Duo [1 ]
Carboni, Bertrand [1 ]
Sortais, Jean-Baptiste [1 ,2 ,3 ]
Darcel, Christophe [1 ]
机构：
[1] Univ Rennes, CNRS, ISCR, UMR 6226, F-35042 Rennes, France
[2] Univ Toulouse, CNRS, LCC, UPS, Toulouse, France
[3] Inst Univ France, 1 Rue Descartes, F-75231 Paris 05, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 19期
关键词：
Iron; alkyne; dehydrogenative borylation; pinacolborane; alkynylboronates; C-H BORYLATION; MARKOVNIKOV-SELECTIVE HYDROBORATION; CROSS-COUPLING REACTIONS; ALKENE HYDROBORATION; METAL; FUNCTIONALIZATION; VINYLARENES; COMPLEXES; BONDS; 1,4-HYDROBORATION;
D O I：
10.1002/adsc.201800588
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The catalytic system based on Fe(OTf)(2) (2.5 mol%) and DABCO (1 mol%) selectively promotes the dehydrogenative borylation of both aromatic and aliphatic terminal alkynes to afford alkynylboronate derivatives in the presence of 1 equiv. of pinacolborane at 100 degrees C in toluene. This methodology is applicable to a variety of terminal alkynes (16 examples, yield: 62-93%).
引用
收藏
页码：3649 / 3654
页数：6
相关论文
共 50 条
  • [41] Development of the First Iron Chloride-Catalyzed Hydration of Terminal Alkynes
    Wu, Xiao-Feng
    Bezier, David
    Darcel, Christophe
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 367 - 370
  • [42] Iron-Catalyzed Synthesis of ß-Chlorovinyl and a,ß-Alkynyl Ketones from Terminal and Silylated Alkynes with Acid Chlorides
    Gandeepan, Parthasarathy
    Parthasarathy, Kanniyappan
    Su, Tsu-Hui
    Cheng, Chien-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) : 457 - 468
  • [43] Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds
    Zeng, Xiaoqin
    Zhang, Yuxuan
    Liu, Zhengli
    Geng, Shasha
    He, Yun
    Feng, Zhang
    ORGANIC LETTERS, 2020, 22 (08) : 2950 - 2955
  • [44] Iron-Catalyzed C?H Fuctionalization of Indoles
    Cai, Yan
    Zhu, Shou-Fei
    Wang, Guo-Peng
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2939 - 2944
  • [45] Iron-Catalyzed Isomerizations of Olefins
    Mayer, Matthias
    Welther, Alice
    Jacobi von Wangelin, Axel
    CHEMCATCHEM, 2011, 3 (10) : 1567 - 1571
  • [46] Organocalcium Complex-Catalyzed Dehydrogenative Coupling of Hydrosilanes with Terminal Alkynes
    Liu, Ruixin
    Liu, Xiaojuan
    Cheng, Tanyu
    Chen, Yaofeng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (01)
  • [47] Mechanism of Iron-Catalyzed C-H Alkenylation of Pivalophenone Derivatives With Unsymmetric Internal Alkynes
    Santoro, Stefano
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2024, 124 (18)
  • [48] Iron-Catalyzed Synthesis of (E)-β-Vinylsilanes via a Regio- and Stereoselective Hydrosilylation from Terminal Alkynes
    Liu, Zhi-Kai
    Zhang, Guo-Liang
    Li, Ding-Chang
    Yang, Ying
    Chen, Li
    Zhan, Zhuang-Ping
    SYNLETT, 2019, 30 (02) : 235 - 239
  • [49] Iron-catalyzed annulation reaction of arylindium reagents and alkynes to produce substituted naphthalenes
    Adak, Laksmikanta
    Yoshikai, Naohiko
    TETRAHEDRON, 2012, 68 (26) : 5167 - 5171
  • [50] Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines
    Lu, Ran
    Cao, Liya
    Guan, Honghao
    Liu, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (15) : 6318 - 6324
12345