A nickel-catalyzed route to pyridines

被引：197

作者：

McCormick, MM ^{[1
]}

Duong, HA ^{[1
]}

Zuo, G ^{[1
]}

Louie, J ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 14期

关键词：

D O I：

10.1021/ja0508931

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and general route for preparing pyridines from nitriles and diynes is described. Ni/imidazolyidene complexes were used to mediate cyclization alkynes and both aryl and alkyl nitriles at ambient temperature. In addition, the efficacy of this protocol allows for the preparation of a fused seven-membered pyridone and for intermolecular cyclizations. When an asymmetrical diyne was employed, cyclization afforded a single pyridine regioisomer. Copyright © 2005 American Chemical Society.

引用

收藏

页码：5030 / 5031

页数：2

相关论文

共 29 条

[1] COUPLING OF 2 ETHYNE MOLECULES AT RHODIUM VERSUS COUPLING OF 2 RHODIUM ATOMS AT ETHYNE .2. IMPLICATIONS FOR THE REACTIVITY - CATALYTIC AND STOICHIOMETRIC FUNCTIONALIZATION REACTIONS OF ETHYNE [J].

BIANCHINI, C ;

MELI, A ;

PERUZZINI, M ;

VACCA, A ;

VIZZA, F .

ORGANOMETALLICS, 1991, 10 (03) :645-651

[2] ORGANOCOBALT COMPOUNDS IN THE SYNTHESIS OF PYRIDINES - AN EXAMPLE OF STRUCTURE-EFFECTIVITY RELATIONSHIPS IN HOMOGENEOUS CATALYSIS [J].

BONNEMANN, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :248-262

[3] ELECTRONIC AND STERIC EFFECTS IN THE RHODIUM-COMPLEX CATALYZED CO-CYCLIZATION OF ALKYNES AND NITRILES TO PYRIDINE-DERIVATIVES [J].

DIVERSI, P ;

ERMINI, L ;

INGROSSO, G ;

LUCHERINI, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 447 (02) :291-298

[4] Nickel-catalyzed cycloaddition of alkynes and isocyanates [J].

Duong, HA ;

Cross, MJ ;

Louie, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11438-11439

[5]

Eisch JJ, 2001, EUR J INORG CHEM, P77

[6] Cobalt-catalyzed alkyne-nitrile cyclotrimerization to form pyridines in aqueous solution [J].

Fatland, AW ;

Eaton, BE .

ORGANIC LETTERS, 2000, 2 (20) :3131-3133

[7] Cleavage of carbon-carbon bonds in alkyl cyanides using nickel(0) [J].

García, JJ ;

Arévalo, A ;

Brunkan, NM ;

Jones, WD .

ORGANOMETALLICS, 2004, 23 (16) :3997-4002

[8] THE CHEMISTRY OF TITANACYCLOPENTADIENE RINGS SUPPORTED BY 2,6-DIPHENYLPHENOXIDE LIGATION - STOICHIOMETRIC AND CATALYTIC REACTIVITY [J].

HILL, JE ;

BALAICH, G ;

FANWICK, PE ;

ROTHWELL, IP .

ORGANOMETALLICS, 1993, 12 (08) :2911-2924

[9] (eta(4)-1,5-cyclooctadiene)(eta(6)-phosphinine)iron(0): Novel room-temperature catalyst for pyridine formation [J].

Knoch, F ;

Kremer, F ;

Schmidt, U ;

Zenneck, U ;

LeFloch, P ;

Mathey, F .

ORGANOMETALLICS, 1996, 15 (12) :2713-2719

[10] Efficient nickel-catalyzed [2+2+2] cycloaddition of CO2 and diynes [J].

Louie, J ;

Gibby, JE ;

Farnworth, MV ;

Tekavec, TN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15188-15189