Cobalt(II) acetylacetonate catalyzed Friedel-Crafts acylation of anisole, thioanisole, and toluene

被引：7

作者：

Tamilselvan, Pitchiah ^{[1
]}

Basavaraju, Yeriyur. B. ^{[2
]}

Murugesan, Ramachandran ^{[3
]}

Sampathkumar, Ellapplan ^{[4
]}

机构：

[1] Reg Inst Educ, DESM, Mysore 570006, Karnataka, India

[2] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India

[3] Biocon India Ltd, Syngene, Bangalore 560110, Karnataka, India

[4] Univ Missouri, Dept Chem, Kansas City, MO 64110 USA

来源：

CATALYSIS COMMUNICATIONS | 2008年 / 10卷 / 03期

关键词：

Cobalt(II) acetylacetonate; Catalysis; Acylation; Anisole; Thioanisole; Nitromethane; Acetonitrile; Solvent effect;

D O I：

10.1016/j.catcom.2008.09.025

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new highly efficient catalytic procedure for the Friedel-Crafts acylation of electron rich aromatics is reported. Cobalt(II) acetylacetonate catalyses the acylation of anisole, thioanisole, and toluene with a variety of acyl chlorides in nitromethane and acetonitrile under mild conditions. The catalyst is found to be reusable and the acylation is regioselective, and affords exclusively C-4 acylated products in excellent yields. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：300 / 303

页数：4

共 24 条

[1] ANHYDROUS HYDROGEN-FLUORIDE CATALYZED FRIEDEL CRAFTS REACTIONS OF THIOAROMATIC COMPOUNDS [J].

ASLAM, M ;

DAVENPORT, KG ;

STANSBURY, WF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5955-5958

[2]

ASLAM M, 1988, Patent No. 4794205

[3] In(III)-mediated chemoselective dehydrogenative interaction of ClMe2SiH with carboxylic acids:: Direct chemo- and regioselective Friedel-Crafts acylation of aromatic ethers [J].

Babu, Srinivasarao Arulananda ;

Yasuda, Makoto ;

Baba, Akio .

ORGANIC LETTERS, 2007, 9 (03) :405-408

[4]

BERNER G, 1986, Patent No. 4582862

[5] Synthesis of trimethyl alpha-keto trithioorthoesters and dimethyl alpha-keto dithioacetals by reaction of acyl chlorides, anhydrides, thiol esters, and N,N-dimethylamides with [tris(methylthio)methyl]lithium [J].

Degani, I ;

Dughera, S ;

Fochi, R ;

Serra, E .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9572-9577

[6] Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis [J].

Dieter, RK .

TETRAHEDRON, 1999, 55 (14) :4177-4236

[7]

DOLLING UH, 1995, Patent No. 5786515

[8]

ERBELE MK, 1980, TETRAHEDRON LETT, P2303

[9] A "hard/soft" mismatch enables catalytic Friedel-Crafts acylations [J].

Fürstner, A ;

Voigtländer, D ;

Schrader, W ;

Giebel, D ;

Reetz, MT .

ORGANIC LETTERS, 2001, 3 (03) :417-420

[10]

GILBERT L, 1997, Patent No. 2238388

← 1 2 3 →