Transition-metal-catalyzed carbonylation of allenes with carbon monoxide and thiols

被引:31
|
作者
Kajitani, Minako
Kamiya, Ikuyo
Nomoto, Akihiro
Kihara, Nobuhiro
Ogawa, Akiya
机构
[1] Osaka Prefecture Univ, Grad Sch Educ, Dept Appl Chem, Naka Ku, Sakai, Osaka 5998531, Japan
[2] Nara Womens Univ, Fac Sci, Dept Chem, Nara 6308506, Japan
[3] Kanagawa Univ, Fac Sci, Dept Chem, Hiratsuka, Kanagawa 2591203, Japan
关键词
carbonylative thiolation; thiol; allene; carbon monoxide; copolymerization;
D O I
10.1016/j.tet.2006.04.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of a catalytic amount of tetrakis(triphenylphosphine)platinum(0), allenes undergo carbonylative thiolation with carbon monoxide and thiols to provide the corresponding alpha,beta- and beta,gamma-unsaturated thioesters in good yields. In contrast, the use of rhodium(I) catalysts such as RhH(CO)(PPh3)(3) in place of Pt(PPh3)(4) leads to copolymerization of allenes and carbon monoxide without incorporation of thio groups. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6355 / 6360
页数:6
相关论文
共 50 条
  • [41] Transition-Metal-Catalyzed Synthesis of Spirolactones
    Mostinski, Yelena
    Lankri, David
    Tsvelikhovsky, Dmitry
    SYNTHESIS-STUTTGART, 2017, 49 (11): : 2361 - 2373
  • [42] Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation
    Petrone, David A.
    Ye, Juntao
    Lautens, Mark
    CHEMICAL REVIEWS, 2016, 116 (14) : 8003 - 8104
  • [43] Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide
    Chen, Yue-Gang
    Xu, Xue-Tao
    Zhang, Kun
    Li, Yi-Qian
    Zhang, Li-Pu
    Fang, Ping
    Mei, Tian-Sheng
    SYNTHESIS-STUTTGART, 2018, 50 (01): : 35 - 48
  • [44] TRANSITION-METAL-CATALYZED ASYMMETRIC CATALYSIS IN SUPERCRITICAL CARBON-DIOXIDE
    FENG, SG
    GROSS, MF
    BURK, MJ
    TUMAS, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 572 - INOR
  • [45] Selective Decarbonylation via Transition-Metal-Catalyzed Carbon- Carbon Bond Cleavage
    Lu, Hong
    Yu, Tian-Yang
    Xu, Peng-Fei
    Wei, Hao
    CHEMICAL REVIEWS, 2021, 121 (01) : 365 - 411
  • [46] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds
    Chen, Feng
    Wang, Teng
    Jiao, Ning
    CHEMICAL REVIEWS, 2014, 114 (17) : 8613 - 8661
  • [47] Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides
    Liu, Ying-Ying
    Sun, Shao-Han
    Min, Xiang-Ting
    Wan, Boshun
    Chen, Qing-An
    SYNTHESIS-STUTTGART, 2022, 54 (11): : 2561 - 2573
  • [48] Calixarene Promoted Transition-Metal-Catalyzed Reactions
    Ma, Zhiyan
    Li, Yunjian
    Sun, Xiao-Qiang
    Yang, Ke
    Li, Zheng-Yi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (06) : 2188 - 2201
  • [49] Transition-metal-catalyzed methods for synthesis of fluorenes
    Kaiser, Reinhard P.
    Caivano, Ilaria
    Kotora, Martin
    TETRAHEDRON, 2019, 75 (22) : 2981 - 2992
  • [50] First-Row Transition-Metal-Catalyzed Carbonylative Transformations of Carbon Electrophiles
    Peng, Jin-Bao
    Wu, Fu-Peng
    Wu, Xiao-Feng
    CHEMICAL REVIEWS, 2019, 119 (04) : 2090 - 2127