Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes

被引:30
作者
Kuang, Zhijie [1 ]
Gao, Guoliang [1 ]
Song, Qiuling [1 ,2 ]
机构
[1] Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Chem Engn, Xiamen 361021, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
base-catalyzed; diborylation of alkynes; cis-1; 2-bis(boryl)alkenes; METAL-FREE DIBORATION; FREE BORYLATION; DIBORON; NANOPARTICLES; ACTIVATION; EFFICIENT; ALKENES;
D O I
10.1007/s11426-018-9344-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.
引用
收藏
页码:62 / 66
页数:5
相关论文
共 51 条
  • [1] a Lee CI, 2015, ANGEW CHEM INT EDIT, V54, P14003, DOI [10.1002/anie.201507372, DOI 10.1002/ANIE.201507372]
  • [2] Synthesis and reactivity of cobalt boryl complexes
    Adams, CJ
    Baber, RA
    Batsanov, AS
    Bramham, G
    Charmant, JPH
    Haddow, MF
    Howard, JAK
    Lam, WH
    Lin, ZY
    Marder, TB
    Norman, NC
    Orpen, AG
    [J]. DALTON TRANSACTIONS, 2006, (11) : 1370 - 1373
  • [3] Solvent-and Ligand-free Diboration of Alkynes and Alkenes Catalyzed by Platinum Nanoparticles on Titania
    Alonso, Francisco
    Moglie, Yanina
    Pastor-Perez, Laura
    Sepulveda-Escribano, Antonio
    [J]. CHEMCATCHEM, 2014, 6 (03) : 857 - 865
  • [4] An experimental and theoretical study into the facile, homogenous (N-heterocyclic carbene)2-Pd(0) catalyzed diboration of internal and terminal alkynes
    Ansell, Melvyn B.
    da Silva, Vitor H. Menezes
    Heerdt, Gabriel
    Braga, Ataualpa A. C.
    Spencer, John
    Navarro, Oscar
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (20) : 7461 - 7467
  • [5] TRANSITION-METAL-CATALYZED DIBORATION OF VINYLARENES
    BAKER, RT
    NGUYEN, P
    MARDER, TB
    WESTCOTT, SA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (12): : 1336 - 1338
  • [6] Hydroxyl-Directed Stereoselective Diboration of Alkenes
    Blaisdell, Thomas P.
    Caya, Thomas C.
    Zhang, Liang
    Sanz-Marco, Amparo
    Morken, James P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (26) : 9264 - 9267
  • [7] Asymmetric organocatalytic diboration of alkenes
    Bonet, Amadeu
    Sole, Cristina
    Gulyas, Henrik
    Fernandez, Elena
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (33) : 6621 - 6623
  • [8] Transition-Metal-Free Diboration Reaction by Activation of Diboron Compounds with Simple Lewis Bases
    Bonet, Amadeu
    Pubill-Ulldemolins, Cristina
    Bo, Caries
    Gulyas, Henrik
    Fernandez, Elena
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) : 7158 - 7161
  • [9] Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration
    Burks, Heather E.
    Kliman, Laura T.
    Morken, James P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) : 9134 - +
  • [10] Remarkable Catalytic Property of Nanoporous Gold on Activation of Diborons for Direct Diboration of Alkynes
    Chen, Qiang
    Zhao, Jian
    Ishikawa, Yoshifumi
    Asao, Naoki
    Yamamoto, Yoshinori
    Jin, Tienan
    [J]. ORGANIC LETTERS, 2013, 15 (22) : 5766 - 5769