A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide

被引:115
作者
Datta, S [1 ]
Chang, CL [1 ]
Yeh, KL [1 ]
Liu, RS [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
关键词
D O I
10.1021/ja036246w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a new and efficient ruthenium-catalyzed reaction that transforms ethynyl alcohol into alkene and carbon monoxide. The most efficient catalysts are TpRu(PPh3)(CH3CN)2PF6 (10 mol %) and lithium triflate (20 mol %). The mechanism of this reaction was elucidated using an isotope-labeling experiment. Copyright © 2003 American Chemical Society.
引用
收藏
页码:9294 / 9295
页数:2
相关论文
共 37 条
[1]   The mechanism of the Ru-assisted C-C bond cleavage of terminal alkynes by water [J].
Bianchini, C ;
Casares, JA ;
Peruzzini, M ;
Romerosa, A ;
Zanobini, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (19) :4585-4594
[2]   Increased activity of in situ catalysts for alkyne metathesis [J].
Brizius, G ;
Bunz, UHF .
ORGANIC LETTERS, 2002, 4 (17) :2829-2831
[3]   Metal vinylidenes in catalysis [J].
Bruneau, C ;
Dixneuf, PH .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) :311-323
[4]  
Bunz UHF, 1999, ANGEW CHEM INT EDIT, V38, P478, DOI 10.1002/(SICI)1521-3773(19990215)38:4<478::AID-ANIE478>3.0.CO
[5]  
2-K
[6]   First X-ray characterization and theoretical study of π-alkyne, alkynyl-hydride, and vinylidene isomers for the same transition metal fragment [Cp*Ru(pEt3)2] [J].
Bustelo, E ;
Carbó, JJ ;
Lledós, A ;
Mereiter, K ;
Puerta, MC ;
Valerga, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (11) :3311-3321
[7]   Reaction of [W(eta(2)-PhC(2)Ph)(3)(NCMe)] with o-diphenylphosphino-styrene and -allylbenzene; Evidence for novel carbon-carbon double and triple bond cleavage and alkyne insertion reactions [J].
Cairns, GA ;
Carr, N ;
Green, M ;
Mahon, MF .
CHEMICAL COMMUNICATIONS, 1996, (21) :2431-2432
[8]   Ethylene and alkyne carbon-carbon bond cleavage across tungsten-tungsten multiple bonds [J].
Chamberlin, RLM ;
Rosenfeld, DC ;
Wolczanski, PT ;
Lobkovsky, EB .
ORGANOMETALLICS, 2002, 21 (13) :2724-2735
[9]   Syntheses and characterization of hydrotris(1-pyrazolyl)borate dihydrogen complexes of ruthenium and their roles in catalytic hydrogenation reactions [J].
Chan, WC ;
Lau, CP ;
Chen, YZ ;
Fang, YQ ;
Ng, SM ;
Jia, GC .
ORGANOMETALLICS, 1997, 16 (01) :34-44
[10]   New water-soluble alkyl-carbonyl iridium complexes containing both Cp* (C5Me5-) and PAr3 (P(m-C6H4SO3Na)3):: Cleavage of C≡C and C=C bonds with water [J].
Chin, CS ;
Chong, D ;
Maeng, B ;
Ryu, J ;
Kim, H ;
Kim, M ;
Lee, H .
ORGANOMETALLICS, 2002, 21 (08) :1739-1742