Acid-promoted olefination of ketones by an iron(III) porphyrin complex

被引：70

作者：

Chen, Y ^{[1
]}

Huang, LY ^{[1
]}

Zhang, XP ^{[1
]}

机构：

[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol0347444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The acid-promoted olefination of unactivated ketones with diazo reagents in the presence of triphenylphosphine can be catalyzed by the commercially available iron(III) porphyrin complex Fe(TPP)Cl. The reactions were effectively carried out under mild conditions in a one-pot fashion with the use of a stoichiometric diazo reagents and substoichiometric benzoic acid. Examples include aromatic, aliphatic, cyclic, and unsaturated ketones with ethyl diazoacetate or tert-butyl diazoacetate.

引用

收藏

页码：2493 / 2496

页数：4

相关论文

共 29 条

[1] Iron(III) and ruthenium(II) porphyrin complex-catalyzed selective olefination of aldehydes with ethyl diazoacetate [J].

Chen, Y ;

Huang, L ;

Ranade, MA ;

Zhang, XP .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3714-3717

[2]

CHEN Y, IN PRESS J ORG CHEM

[3] Iron porphyrin-catalyzed olefination of carbonyl compounds with ethyl diazoacetate [J].

Cheng, GL ;

Mirafzal, GA ;

Woo, LK .

ORGANOMETALLICS, 2003, 22 (07) :1468-1474

[4] SYNTHETIC APPLICATIONS OF METALATED PHOSPHONIUM YLIDES [J].

CRISTAU, HJ .

CHEMICAL REVIEWS, 1994, 94 (05) :1299-1313

[5]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[6] Recent advances in asymmetric catalytic metal carbene transformations [J].

Doyle, MP ;

Forbes, DC .

CHEMICAL REVIEWS, 1998, 98 (02) :911-935

[7] Olefination of aldehydes by ethyl diazoacetate catalyzed by a ruthenium(II) complex [J].

Fujimura, O ;

Honma, T .

TETRAHEDRON LETTERS, 1998, 39 (07) :625-626

[8] Structural characterization and catalytic activity of the rhodium-carbene complex Rh(PPh3)2(IMes)Cl (IMes = bis(1,3-(2,4,6-trimethylphenyl)imidazol-2-ylidene) [J].

Grasa, GA ;

Moore, Z ;

Martin, KL ;

Stevens, ED ;

Nolan, SP ;

Paquet, V ;

Lebel, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 658 (1-2) :126-131

[9] MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .135. OXORHENIUM(V) CATALYSTS FOR THE OLEFINATION OF ALDEHYDES [J].

HERRMANN, WA ;

ROESKY, PW ;

WANG, M ;

SCHERER, W .

ORGANOMETALLICS, 1994, 13 (11) :4531-4535

[10] MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .100. METHYLTRIOXORHENIUM AS CATALYST OF A NOVEL ALDEHYDE OLEFINATION [J].

HERRMANN, WA ;

WANG, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1641-1643