Catalytic Reductive Vinylidene Transfer Reactions

被引:53
作者
Pal, Sudipta [1 ]
Zhou, You-Yun [1 ]
Uyeda, Christopher [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
基金
美国国家科学基金会;
关键词
BUTTENBERG-WIECHELL REARRANGEMENT; DINUCLEAR NICKEL-COMPLEXES; ALKYLIDENECYCLOPROPANE DERIVATIVES; UNSATURATED CARBENES; METAL VINYLIDENES; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; CHEMISTRY; ALKYLIDENECARBENES; METHYLENECYCLOPROPANES;
D O I
10.1021/jacs.7b05901
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Methylenecyclopropanes are important synthetic intermediates that possess strain energies exceeding those of saturated cyclopropanes by >10 kcal/mol. This report describes a catalytic reductive methylenecyclopropanation reaction of simple olefins, utilizing 1,1-dichloroalkenes as vinylidene precursors. The reaction is promoted by a dinuclear Ni catalyst, which is proposed to access Ni-2(vinylidenoid) intermediates via C-Cl oxidative addition.
引用
收藏
页码:11686 / 11689
页数:4
相关论文
共 49 条
  • [1] [Anonymous], J LIEBIGS ANN CHEM, DOI DOI 10.1002/JLAC.18942790310
  • [2] Synthesis of Methylene- and Alkylidenecyclopropane Derivatives
    Audran, Gerard
    Pellissier, Helene
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) : 575 - 608
  • [3] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands
    Bigeault, J
    Giordano, L
    Buono, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) : 4753 - 4757
  • [4] REACTIONS OF METHYLENECYCLOPROPANES .7. NICKEL(O)-CATALYZED CYCLO-ADDITIONS OF METHYLENECYCLOPROPANES WITH ALKYL ACRYLATES
    BINGER, P
    BRINKMANN, A
    WEDEMANN, P
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (08): : 2920 - 2930
  • [5] Synthesis of methylene- and alkylidenecyclopropane derivatives
    Brandi, A
    Goti, A
    [J]. CHEMICAL REVIEWS, 1998, 98 (02) : 589 - 635
  • [6] Progress in the Synthesis and Transformations of Alkylidenecyclopropanes and Alkylidenecyclobutanes
    Brandi, Alberto
    Cicchi, Stefano
    Cordero, Franca M.
    Goti, Andrea
    [J]. CHEMICAL REVIEWS, 2014, 114 (15) : 7317 - 7420
  • [7] ORGANOMETALLIC CHEMISTRY OF VINYLIDENE AND RELATED UNSATURATED CARBENES
    BRUCE, MI
    [J]. CHEMICAL REVIEWS, 1991, 91 (02) : 197 - 257
  • [8] Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis
    Bruneau, C
    Dixneuf, PH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2176 - 2203
  • [9] Metal vinylidenes in catalysis
    Bruneau, C
    Dixneuf, PH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) : 311 - 323
  • [10] Bruneau C., 2008, METAL VINYLIDENES AL