Palladium-catalyzed azathiolation of carbon monoxide

被引:34
作者
Kuniyasu, H [1 ]
Hiraike, H [1 ]
Morita, M [1 ]
Tanaka, A [1 ]
Sugoh, K [1 ]
Kurosawa, H [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan
关键词
D O I
10.1021/jo9823137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel palladium-catalyzed azathiolation of carbon monoxide using sulfenamide (RSNR'(2)) (1) is described to provide thiocarbamate 2 in good yields. The mechanistic proposal includes the following: (1) insertion of CO into Pd-S bond of Pd(SR)(2)(PPh3)(n) 4 to provide Pd[C(O)SR](SR)-(PPh3)(n) 5 and (2) sigma-bond metathesis between S-N and Pd-C(O) bonds to afford 2 with the regeneration of 4.
引用
收藏
页码:7305 / 7308
页数:4
相关论文
共 48 条
  • [21] First transition-metal complex catalyzed addition of organic disulfides to alkenes enables the rapid synthesis of vicinal-dithioethers
    Kondo, T
    Uenoyama, SY
    Fujita, K
    Mitsudo, TA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) : 482 - 483
  • [22] THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED HYDROSELENATION OF ACETYLENES
    KUNIYASU, H
    OGAWA, A
    SATO, KI
    RYU, I
    SONODA, N
    [J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5525 - 5528
  • [23] PALLADIUM-CATALYZED ADDITION AND CARBONYLATIVE ADDITION OF DIARYL DISULFIDES AND DISELENIDES TO TERMINAL ACETYLENES
    KUNIYASU, H
    OGAWA, A
    MIYAZAKI, SI
    RYU, I
    KAMBE, N
    SONODA, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) : 9796 - 9803
  • [24] THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED ADDITION OF AROMATIC THIOLS TO ACETYLENES
    KUNIYASU, H
    OGAWA, A
    SATO, KI
    RYU, I
    KAMBE, N
    SONODA, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5902 - 5903
  • [25] The first evidence of insertion of isocyanide into a metal-sulfur bond: Catalytic and stoichiometric behavior of isocyanide and thiolate ligands on palladium and platinum
    Kuniyasu, H
    Sugoh, K
    Su, MS
    Kurosawa, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) : 4669 - 4677
  • [26] Formation of [CoPt2Cl2(PPh(3))(4)(mu(3)-S)(2)] from facile heterometallation of [Pt-2(PPh(3))(4)(mu-S)(2)] and its facile deheterometallation via carbonylative desulfurization to give Pt-Pt bonded [Pt-2(CO)(2)(PPh(3))(2)(mu-S)]
    Liu, H
    Tan, AL
    Mok, KF
    Hor, TSA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (20): : 4023 - 4026
  • [27] LUH TY, 1990, SYNTHESIS-STUTTGART, P89
  • [28] Carbon-sulfur bond-forming reductive elimination involving sp-, sp2-, and sp3-hybridized carbon.: Mechanism, steric effects, and electronic effects on sulfide formation
    Mann, G
    Baranano, D
    Hartwig, JF
    Rheingold, AL
    Guzei, IA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) : 9205 - 9219
  • [29] THIANICKELACYCLES BY RING-OPENING REACTIONS OF CYCLIC THIOETHERS AND THEIR SUBSEQUENT CARBONYLATION TO THIOESTERS
    MATSUNAGA, PT
    HILLHOUSE, GL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (17): : 1748 - 1749
  • [30] Palladium-catalyzed hydroselenation of allenes with benzeneselenol
    Ogawa, A
    Kudo, A
    Hirao, T
    [J]. TETRAHEDRON LETTERS, 1998, 39 (29) : 5213 - 5216