Discovery of and mechanistic insight into a ligand-modulated palladium-catalyzed Wacker oxidation of styrenes using TBHP

被引:127
作者
Cornell, CN [1 ]
Sigman, MS [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
D O I
10.1021/ja043203m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe the discovery of a new N-heterocyclic carbene-modulated Pd catalyst for the Wacker oxidation that does not require molecular oxygen but instead uses TBHP as a reagent in this oxidation. The catalyst activity and selectivity for the oxidation of styrene derivatives to methyl ketones are among the best reported. Preliminary mechanistic studies of the catalytic system were performed and show that the origin of the carbonyl oxygen is TBHP and that the hydrogens in the product all originate from the starting olefin. Copyright © 2005 American Chemical Society.
引用
收藏
页码:2796 / 2797
页数:2
相关论文
共 15 条
  • [1] ALANDIS N, 1994, NEW J CHEM, V18, P1147
  • [2] DUAL-FUNCTION PHASE-TRANSFER CATALYSIS IN THE METAL-ASSISTED OXIDATION BY HYDROGEN-PEROXIDE OF STYRENE TO BENZALDEHYDE OR ACETOPHENONE
    BARAK, G
    SASSON, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (16) : 1266 - 1267
  • [3] PALLADIUM(II) TERT-BUTYL PEROXIDE CARBOXYLATES - NEW REAGENTS FOR THE SELECTIVE OXIDATION OF TERMINAL OLEFINS TO METHYL KETONES - ROLE OF PEROXYMETALATION IN SELECTIVE OXIDATIVE PROCESSES
    MIMOUN, H
    CHARPENTIER, R
    MITSCHLER, A
    FISCHER, J
    WEISS, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) : 1047 - 1054
  • [4] Elucidating the significance of β-hydride elimination and the dynamic role of acid/base chemistry in a palladium-catalyzed aerobic oxidation of alcohols
    Mueller, JA
    Goller, CP
    Sigman, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9724 - 9734
  • [5] Selective oxidation of styrene to acetophenone in the presence of ionic liquids
    Namboodiri, VV
    Varma, RS
    Sahle-Demessie, E
    Pillai, UR
    [J]. GREEN CHEMISTRY, 2002, 4 (02) : 170 - 173
  • [6] NISHIMURA T, 2000, J CHEM SOC P1, V12, P1915
  • [7] PALLADIUM-CATALYZED OXIDATION OF TERMINAL OLEFINS TO METHYL KETONES BY HYDROGEN-PEROXIDE
    ROUSSEL, M
    MIMOUN, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26) : 5387 - 5390
  • [8] Sharpless K.B., 1979, ALDRICHIM ACTA, V12, P63
  • [9] SMIDT J, 1962, CHEM IND-LONDON, P54
  • [10] AEROBIC OXIDATION OF ETHERS AND ALKENES CATALYZED BY A NOVEL PALLADIUM COMPLEX
    SOMMOVIGO, M
    ALPER, H
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1994, 88 (02): : 151 - 158