Conjugate addition of alcohols to acrylic compounds catalyzed by a bifunctional ruthenium-acetamido complex

被引:34
作者
Yi, CS [1 ]
Yun, SY [1 ]
He, ZJ [1 ]
机构
[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA
关键词
D O I
10.1021/om030418g
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The ruthenium-acetamido complex [(PCy3)(2)-(CO)(CH3CONH)(i-PrOH)RuH] (1) was found to be an effective catalyst for the conjugate addition of alcohols to acrylic compounds under mild reaction conditions to form beta-alkoxynitrile compounds. The bifunctional activity of 1 from the Lewis acid ruthenium center for facilitating N-coordination of acrylonitrile and the basic amido ligand for mediating heterolytic alcohol O-H bond cleavage have been proposed for the catalytic reaction.
引用
收藏
页码:3031 / 3033
页数:3
相关论文
共 28 条
[1]  
ENDERS D, 1995, ANGEW CHEM INT EDIT, V34, P455, DOI 10.1002/anie.199504551
[2]   C-13 kinetic isotope effects for the addition of lithium dibutylcuprate to cyclohexenone. Reductive elimination is rate-determining [J].
Frantz, DE ;
Singleton, DA ;
Snyder, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3383-3384
[3]   Michael reaction of stabilized carbon nucleophiles catalyzed by [RuH2(PPh(3))(4)] [J].
GomezBengoa, E ;
Cuerva, JM ;
Mateo, C ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) :8553-8565
[4]   The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].
Haack, KJ ;
Hashiguchi, S ;
Fujii, A ;
Ikariya, T ;
Noyori, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288
[5]   Effects of phosphine ligand chelation on the reactivity of monomeric parent amido ruthenium complexes: Synthesis and reactivity of such a complex bearing monodentate ligands [J].
Holland, AW ;
Bergman, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14684-14695
[6]   The binuclear iridium(II) hydride complex [(C5Me5)Ir(μ-H)]2:: A novel base for reversible deprotonation of acidic organic compounds and a unique catalyst for C-C bond cleavage of aromatic 1,2-diols and Michael additions [J].
Hou, ZM ;
Koizumi, TA ;
Fujita, A ;
Yamazaki, H ;
Wakatsuki, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5812-5813
[7]  
JUNG ME, 1991, COMPREHENSIVE ORGANI
[8]   Transition metal-catalyzed addition of amines to acrylic acid derivatives. A high-throughput method for evaluating hydroamination of primary and secondary alkylamines [J].
Kawatsura, M ;
Hartwig, JF .
ORGANOMETALLICS, 2001, 20 (10) :1960-1964
[9]  
Kempe R, 2000, ANGEW CHEM INT EDIT, V39, P468, DOI 10.1002/(SICI)1521-3773(20000204)39:3<468::AID-ANIE468>3.0.CO
[10]  
2-G