Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex

被引：28

作者：

Bai, CX ^{[1
]}

Lu, XB ^{[1
]}

He, R ^{[1
]}

Zhang, WZ ^{[1
]}

Feng, XJ ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 22期

关键词：

D O I：

10.1039/b510776h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The exchange of the PPh3 ligand in the complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene](PPh3)-(Cl)(2)Ru=CHPh (7) for a pyridine ligand at ambient temperature leads to the formation of the stable phosphine-free carbene ruthenium complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene](C5H5N)(2)(Cl)(2) Ru=CHPh (8). The resulted ruthenium complex exhibits highly catalytic activity for the cross metathesis of acrylonitrile with various functionalized olefins under mild conditions, and its activity can be further improved by the addition of a Lewis acid such as Ti(O'Pr)(4). In the mixture products, the Z-isomer predominates.

引用

页码：4139 / 4142

页数：4

共 34 条

[1]

Armstrong S, 1998, J CHEM SOC P1, V1, P317

[2] LIVING RING-OPENING METATHESIS POLYMERIZATION OF 2,3-DIFUNCTIONALIZED NORBORNADIENES BY MO(CH-TERT-BU)(N-2,6-C6H3-ISO-PR2)(O-TERT-BU)2 [J].

BAZAN, GC ;

KHOSRAVI, E ;

SCHROCK, RR ;

FEAST, WJ ;

GIBSON, VC ;

OREGAN, MB ;

THOMAS, JK ;

DAVIS, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8378-8387

[3] LIVING RING-OPENING METATHESIS POLYMERIZATION OF 2,3-DIFUNCTIONALIZED 7-OXANORBORNENES AND 7-OXANORBORNADIENES BY MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(O-TERT-BU)2 AND MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(OCME2CF3)2 [J].

BAZAN, GC ;

OSKAM, JH ;

CHO, HN ;

PARK, LY ;

SCHROCK, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :6899-6907

[4] Reaction between ruthenium(0) complexes and dihalo compounds. A new method for the synthesis of ruthenium olefin metathesis catalysts [J].

Belderrain, TR ;

Grubbs, RH .

ORGANOMETALLICS, 1997, 16 (18) :4001-4003

[5] New approaches to olefin cross-metathesis [J].

Blackwell, HE ;

O'Leary, DJ ;

Chatterjee, AK ;

Washenfelder, RA ;

Bussmann, DA ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71

[6] Synthesis of functionalized olefins by cross and ring-closing metatheses [J].

Chatterjee, AK ;

Morgan, JP ;

Scholl, M ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784

[7] Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].

Chatterjee, AK ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (11) :1751-1753

[8] Recent developments in olefin cross-metathesis [J].

Connon, SJ ;

Blechert, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923

[9] Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols (vol 624, pg 327, 2001) [J].

Cossy, J ;

BouzBouz, S ;

Hoveyda, AH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (02) :215-221

[10] ACRYLONITRILE CROSS-METATHESIS - COAXING OLEFIN METATHESIS REACTIVITY FROM A RELUCTANT SUBSTRATE [J].

CROWE, WE ;

GOLDBERG, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (18) :5162-5163

← 1 2 3 4 →