Two types of rhodium-catalyzed CS/CS metathesis reactions: formation of CS/CS bonds and CC/SS bonds

被引:10
作者
Arisawa, Mieko [1 ]
Tagami, Yoko [1 ]
Yamaguchi, Masahiko [1 ,2 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, WPI Adv Inst Mat Res, Sendai, Miyagi 9808578, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/j.tetlet.2008.01.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium complex catalyzes two types of single bond metathesis reactions of two CS bonds depending on the added ligand: CS/CS to CS/CS metathesis and CS/CS to CC/SS metathesis. In the presence of a catalytic amount of RhH(PPh3)(4) and 1,1 '-bis(diphenylphosphino)ferrocene (dppf), two 1-alkylthioalkynes exchange alkylthio groups to give equilibrium mixtures of four 1-alkylthioalkynes. When tris(p-methoxyphenyl)phosphine or diphenylmethylphosphine is used, 1,3-butadiynes are obtained. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1593 / 1597
页数:5
相关论文
共 17 条
[1]   RhCl3-catalyzed disulfide exchange reaction using water solvent in homogeneous and heterogeneous systems [J].
Arisawa, M ;
Suwa, A ;
Yamaguchi, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) :1159-1168
[2]   Equilibrating C-S bond formation by C-H and S-S bond metathesis. Rhodium-catalyzed alkylthiolation reaction of 1-alkynes with disulfides [J].
Arisawa, M ;
Fujimoto, K ;
Morinaka, S ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12226-12227
[3]   Rhodium-catalyzed thiophosphinylation and phosphinylation reactions of disulfides and diselenides [J].
Arisawa, M ;
Ono, T ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2005, 46 (34) :5669-5671
[4]   Oxidation/reduction interconversion of thiols and disulfides using hydrogen and oxygen catalyzed by a rhodium complex [J].
Arisawa, M ;
Sugata, C ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2005, 46 (36) :6097-6099
[5]   Rhodium-catalyzed sulfur atom exchange reaction between organic polysulfides and sulfur [J].
Arisawa, M ;
Tanaka, K ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2005, 46 (28) :4797-4800
[6]   Rhodium-catalyzed disulfide exchange reaction [J].
Arisawa, M ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6624-6625
[7]  
ARISAWA M, IN PRESS PURE APPL C
[8]  
ARISAWA M, 2007, SYNTH ORG CHEM JPN, V65, P1213
[9]  
AYE KT, 1989, ORGANOMETALLICS, V8, P1518
[10]   SYNTHESIS AND STUDY OF THE BENZYLPALLADIUM(IV) AND NAPHTHYLPALLADIUM(IV) COMPLEXES PDBRME2(CH2AR) (BPY2), PDBRME2(CH2AR) (PHEN2) AND MU-HYDROCARBYL PALLADIUM(IV)-PALLADIUM(IV) AND PALLADIUM(IV) PLATINUM(IV) COMPLEXES AND THE STRUCTURE OF FAC-PDBRME2(CH2-P-C6H4BR) (PHEN) [J].
BYERS, PK ;
CANTY, AJ ;
SKELTON, BW ;
TRAILL, PR ;
WATSON, AA ;
WHITE, AH .
ORGANOMETALLICS, 1990, 9 (12) :3080-3085