Ruthenium-catalyzed propargylic substitution reaction of propargylic alcohols with thiols: A general synthetic route to propargylic sulfides

被引:120
作者
Inada, Y
Nishibayashi, Y
Hidai, M
Uemura, S [1 ]
机构
[1] Sci Univ Tokyo, Dept Mat Sci & Technol, Noda, Chiba 2788510, Japan
[2] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1021/ja027754t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel cationic methanethiolate-bridged diruthenium complex [Cp*RuCl(μ2-SMe)2RuCp*(OH2)]OTf (1e) has been disclosed to promote the catalytic propargylic substitution reaction of propargylic alcohols bearing not only terminal alkyne group but also internal alkyne group with thiols. It is noteworthy that neutral thiolate-bridged diruthenium complexes (1a-1c), which were known to promote the propargylic substitution reactions of propargylic alcohols bearing a terminal alkyne group with various heteroatom- and carbon-centered nucleophiles, did not work at all. The catalytic reaction described here provides a general and environmentally friendly preparative method for propargylic sulfides, which are quite useful intermediates in organic synthesis, directly from the corresponding propargylic alcohols and thiols. Copyright © 2002 American Chemical Society.
引用
收藏
页码:15172 / 15173
页数:2
相关论文
共 20 条
[11]   Ir-catalyzed substitution of propargylic-type esters with enoxysilanes [J].
Matsuda, I ;
Komori, K ;
Itoh, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) :9072-9073
[12]   CHEMISTRY AND SYNTHETIC UTILITY OF COBALT-COMPLEXED PROPARGYL CATIONS [J].
NICHOLAS, KM .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (06) :207-214
[13]   Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols [J].
Nishibayashi, Y ;
Yoshikawa, M ;
Inada, Y ;
Hidai, M ;
Uemura, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11846-11847
[14]   Novel propargylic substitution reactions catalyzed by thiolate-bridged diruthenium complexes via allenylidene intermediates [J].
Nishibayashi, Y ;
Wakiji, I ;
Hidai, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11019-11020
[15]  
Nishibayashi Y, 2000, ANGEW CHEM INT EDIT, V39, P2909, DOI 10.1002/1521-3773(20000818)39:16<2909::AID-ANIE2909>3.3.CO
[16]  
2-I
[17]   Ruthenium-catalyzed propargylic alkylation of propargylic alcohols with ketones:: Straightforward synthesis of γ-keto acetylenes [J].
Nishibayashi, Y ;
Wakiji, I ;
Ishii, Y ;
Uemura, S ;
Hidai, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3393-3394
[18]  
Reddy TI, 1997, CHEM COMMUN, P621
[19]   PROPARGYL COMPLEXES OF RUTHENIUM [J].
SHUCHART, CE ;
WILLIS, RR ;
WOJCICKI, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 424 (02) :185-198
[20]   Allenyls and propargyls: versatile ligands in ransition-metal chemistry [J].
Wojcicki, A .
INORGANIC CHEMISTRY COMMUNICATIONS, 2002, 5 (01) :82-97