Platinum-catalyzed highly selective thiocarbonylation of acetylenes with thiols and carbon monoxide

被引:47
作者
Kawakami, J
Mihara, M
Kamiya, I
Takeba, M
Ogawa, A [1 ]
Sonoda, N
机构
[1] Nara Womens Univ, Fac Sci, Dept Chem, Nara 6308506, Japan
[2] Takeda Chem Ind Ltd, Chem Dev Labs, Yodogawa Ku, Osaka 5328686, Japan
[3] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[4] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5640073, Japan
关键词
thiocarbonylation; platinum; thiols; carbon monoxide; acetylenes;
D O I
10.1016/S0040-4020(03)00485-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel carbonylative addition of thiols (RSH) to terminal acetylenes (R!-Cequivalent toCH) takes place successfully in the presence of platinum catalysts under the pressure of carbon monoxide, providing alpha,beta-unsaturated thioesters (R'-C(C(O)SR)=CH2) in good yields regioselectively. This 'hydrothiocarbonylation' reaction of acetylenes may include the formation of the platinum sulfide complex as key species. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3521 / 3526
页数:6
相关论文
共 76 条
[21]   Metal-catalyzed carbon-sulfur bond formation [J].
Kondo, T ;
Mitsudo, T .
CHEMICAL REVIEWS, 2000, 100 (08) :3205-3220
[22]   Ruthenium-catalyzed S-propargylation of thiols enables the rapid synthesis of propargylic sulfides [J].
Kondo, T ;
Kanda, Y ;
Baba, A ;
Fukuda, K ;
Nakamura, A ;
Wada, K ;
Morisaki, Y ;
Mitsudo, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :12960-12961
[23]   Novel catalytic performance of ruthenium complexes for organic synthesis [J].
Kondo, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2001, 59 (03) :170-184
[24]   First transition-metal complex catalyzed addition of organic disulfides to alkenes enables the rapid synthesis of vicinal-dithioethers [J].
Kondo, T ;
Uenoyama, SY ;
Fujita, K ;
Mitsudo, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :482-483
[25]   First ruthenium-catalyzed allylation of thiols enables the general synthesis of allylic sulfides [J].
Kondo, T ;
Morisaki, Y ;
Uenoyama, S ;
Wada, K ;
Mitsudo, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) :8657-8658
[26]  
Kuniyasu H, 2002, CHEM-EUR J, V8, P2661
[27]   PALLADIUM-CATALYZED ADDITION AND CARBONYLATIVE ADDITION OF DIARYL DISULFIDES AND DISELENIDES TO TERMINAL ACETYLENES [J].
KUNIYASU, H ;
OGAWA, A ;
MIYAZAKI, SI ;
RYU, I ;
KAMBE, N ;
SONODA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9796-9803
[28]   THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED ADDITION OF AROMATIC THIOLS TO ACETYLENES [J].
KUNIYASU, H ;
OGAWA, A ;
SATO, KI ;
RYU, I ;
KAMBE, N ;
SONODA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5902-5903
[29]  
Kuniyasu H., 2001, CATALYTIC HETEROFUNC, P217
[30]  
LAUTENS M, 2001, SCI SYNTHESIS, V1, P1