Phosphine-free cationic rhodium(I) complex-catalyzed disulfide exchange reaction: convenient synthesis of unsymmetrical disultides

被引:65
作者
Tanaka, K [1 ]
Ajiki, K [1 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Tokyo 1848588, Japan
关键词
disulfide; disulfide exchange; phosphine-free; rhodium;
D O I
10.1016/j.tetlet.2004.05.092
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A phosphine-free cationic rhodium(I) complex, [Rh(cod)(2)]BF4, is an effective catalyst for disulfide exchange reaction of symmetrical disulfides to unsymmetrical disulfides under inert atmosphere. This reaction could be carried out using unpurified commercial grade solvents under air without decrease of yields and reaction rates. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5677 / 5679
页数:3
相关论文
共 35 条
[1]   Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support [J].
Ali, MH ;
McDermott, M .
TETRAHEDRON LETTERS, 2002, 43 (35) :6271-6273
[2]   Rhodium-catalyzed disulfide exchange reaction [J].
Arisawa, M ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6624-6625
[3]  
ARMITAGE DA, 1972, J CHEM SOC P1, P860
[4]   N-trifluoroacetyl arenesulfenamides, effective precursors for synthesis of unsymmetrical disulfides and sulfenamides [J].
Bao, M ;
Shimizu, M .
TETRAHEDRON, 2003, 59 (48) :9655-9659
[5]  
Barnum, 1970, J AM CHEM SOC, V92, P7629, DOI 10.1021/ja00729a042
[6]   Element-element addition to alkynes catalyzed by the group 10 metals [J].
Beletskaya, I ;
Moberg, C .
CHEMICAL REVIEWS, 1999, 99 (12) :3435-3461
[7]   THE MECHANISM OF DISULFIDE INTERCHANGE IN ACID SOLUTION - ROLE OF SULFENIUM IONS [J].
BENESCH, RE ;
BENESCH, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (07) :1666-1669
[8]  
BOUSTANY KS, 1970, TETRAHEDRON LETT, P3547
[9]  
Cremlyn R. J., 1996, INTRO ORGANOSULFUR C
[10]  
DAHLMAN G, 1964, J ORG CHEM, V29, P1480