A protic additive suppresses formation of byproducts in platinum-catalyzed hydrophosphination of activated olefins. Evidence for P-C and C-C bond formation by Michael addition

被引:96
作者
Scriban, C [1 ]
Kovacik, I [1 ]
Glueck, DS [1 ]
机构
[1] Dartmouth Coll, Dept Chem, Burke Lab 6128, Hanover, NH 03755 USA
关键词
D O I
10.1021/om050433g
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Platinum-catalyzed hydrophosphination of activated olefins yields byproducts derived from more than one alkene. Formation of byproducts is suppressed by adding tert-butyl alcohol, consistent with a mechanism in which Michael addition of a nucleophilic Pt-PR2 group to the alkene yields a zwitterionic intermediate, which can undergo further conjugate additions.
引用
收藏
页码:4871 / 4874
页数:4
相关论文
共 25 条
  • [1] A SHORT LARGE-SCALE SYNTHESIS OF (+/-)SARKOMYCIN ESTERS
    AMRI, H
    RAMBAUD, M
    VILLIERAS, J
    [J]. TETRAHEDRON LETTERS, 1989, 30 (52) : 7381 - 7382
  • [2] CYCLOADDITION OF ALKENES AND ALKYNES TO CPFE(CO)2PR2 TO GIVE (R)2PFEC(=O)C=C HETEROMETALLACYCLES
    ASHBY, MT
    ENEMARK, JH
    [J]. ORGANOMETALLICS, 1987, 6 (06) : 1323 - 1327
  • [3] ELECTROLYTIC REDUCTIVE COUPLING .8. UTILIZATION AND A NEW PREPARATION OF ALPHA-METHYLENEGLUTARONITRILE
    BAIZER, MM
    ANDERSON, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) : 1357 - &
  • [4] Recent advances in the Baylis-Hillman reaction and applications
    Basavaiah, D
    Rao, AJ
    Satyanarayana, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
  • [7] Chemoselective platinum(0)-catalysed hydrophosphination of ethyl acrylate
    Costa, E
    Pringle, PG
    Worboys, K
    [J]. CHEMICAL COMMUNICATIONS, 1998, (01) : 49 - 50
  • [8] Self-replication of tris(cyanoethyl)phosphine catalysed by platinum group metal complexes
    Costa, E
    Pringle, PG
    Smith, MB
    Worboys, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (22): : 4277 - 4282
  • [9] Activation of ancillary ligands in the reactions of DMAD with phosphido and alkylideneamido rhenium complexes
    Cuesta, L
    Hevia, E
    Morales, D
    Pérez, J
    Riera, V
    Seitz, M
    Miguel, D
    [J]. ORGANOMETALLICS, 2005, 24 (07) : 1772 - 1775
  • [10] Activation of a 1,10-phenanthroline ligand on a rhenium tricarbonyl complex
    Cuesta, L
    Hevia, E
    Morales, D
    Pérez, J
    Riera, V
    Rodríguez, E
    Miguel, D
    [J]. CHEMICAL COMMUNICATIONS, 2005, (01) : 116 - 117