Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes

被引:47
|
作者
Shibata, Yu [1 ]
Hirano, Masao [1 ]
Tanaka, Ken [1 ]
机构
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan
关键词
D O I
10.1021/ol800995r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cationic rhodium(I)/H(8)-BINAP complex catalyzes codimerization of alkenes bearing no alpha-hydrogen and electron-deficient internal alkynes, leading to 1,3-dienes in good yields with moderate to excellent regio- and stereoselectivity. The same complex also catalyzes codimerization of an acrylate and phenyl-substituted electron-rich internal alkynes, leading to 1,3-dienes.
引用
收藏
页码:2829 / 2831
页数:3
相关论文
共 50 条
  • [31] Cross-metathesis of 1,3-dienes with electron-deficient olefins
    Dewi, P
    Randl, S
    Blechert, S
    TETRAHEDRON LETTERS, 2005, 46 (04) : 577 - 580
  • [32] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Yang, Hui
    Yang, Zi-Qi
    Zhang, Su-Zhen
    Zhang, Wen-Wen
    Gu, Qing
    You, Shu-Li
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (10) : 2842 - 2846
  • [33] Platinum-catalyzed silaborative coupling of 1,3-dienes to aldehydes: Regio- and stereoselective allylation with dienes through allylic platinum intermediates
    Suginome, M
    Nakamura, H
    Matsuda, T
    Ito, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (17) : 4248 - 4249
  • [34] Mechanism of regioselectivity of rhodium-catalyzed hydrothiolation of 1,3-dienes: A computational study
    Yu, Xianjie
    Shen, Xinyu
    Liu, Shengnan
    Wang, Wenjuan
    Wang, Qiong
    Liu, Jianbiao
    Chen, Dezhan
    MOLECULAR CATALYSIS, 2021, 515
  • [35] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Hui Yang
    Zi-Qi Yang
    Su-Zhen Zhang
    Wen-Wen Zhang
    Qing Gu
    Shu-Li You
    Science China(Chemistry), 2023, (10) : 2842 - 2846
  • [36] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Hui Yang
    Zi-Qi Yang
    Su-Zhen Zhang
    Wen-Wen Zhang
    Qing Gu
    Shu-Li You
    Science China Chemistry, 2023, 66 : 2842 - 2846
  • [37] Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst
    Ping Zhang
    Wenju Chang
    Hongyun Jiao
    Yanshang Kang
    Wenxuan Zhao
    Peipei Cui
    Yong Liang
    Wei-Yin Sun
    Yi Lu
    Chinese Chemical Letters, 2021, 32 (05) : 1717 - 1720
  • [38] Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst
    Zhang, Ping
    Chang, Wenju
    Jiao, Hongyun
    Kang, Yanshang
    Zhao, Wenxuan
    Cui, Peipei
    Liang, Yong
    Sun, Wei-Yin
    Lu, Yi
    CHINESE CHEMICAL LETTERS, 2021, 32 (05) : 1717 - 1720
  • [39] Rhodium(I)-catalyzed [4+2+2] cycloadditions of 1,3-dienes, alkenes, and alkynes for the synthesis of cyclooctadienes
    Wender, PA
    Christy, JP
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) : 5354 - 5355
  • [40] Regio-, Chemo-, and Enantioselective Ni-Catalyzed Hydrocyanation of 1,3-Dienes
    Yu, Rongrong
    Xing, Yidan
    Fang, Xianjie
    ORGANIC LETTERS, 2021, 23 (03) : 930 - 935