Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

被引：51

作者：

Kotti, SRSS ^{[1
]}

Xu, X ^{[1
]}

Wang, YN ^{[1
]}

Headley, AD ^{[1
]}

Li, GG ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 39期

基金：

美国国家卫生研究院;

关键词：

aminohalogenation; ionic liquid; cinnamates; copper(I)triflate;

D O I：

10.1016/j.tetlet.2004.08.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl2 proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol%). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7209 / 7212

页数：4

共 33 条

[1] REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .9. NEW REAGENTS FOR AMINATION OF ETHYLENIC LINKAGE [J].

BARTON, DHR ;

BRITTENKELLY, MR ;

FERREIRA, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (09) :1090-1100

[2]

Chen DJ, 2004, EUR J ORG CHEM, V2004, P3097

[3] EVIDENCE FOR NUCLEOPHILICITY OF OXYGEN ATOMS OF NN-DIHALOGENOSULPHONAMIDES IN ADDITION OF NN-DICHLOROBENZENESULPHONAMIDE TO CIS- AND TRANS-BUT-2-ENE [J].

DANIHER, FA ;

MELCHIOR, MT ;

BUTLER, PE .

CHEMICAL COMMUNICATIONS, 1968, (16) :931-&

[4] ADDITION OF N,N-DICHLOROSULFONAMIDES TO UNSATURATES [J].

DANIHER, FA ;

BUTLER, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (12) :4336-&

[5] ADDITION OF N,N-DICHLORO CARBAMATES TO CONJUGATED DIENES [J].

DANIHER, FA ;

BUTLER, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (07) :2637-&

[6] CHROMOUS CHLORIDE PROMOTED ADDITION OF N-HALOAMIDES TO OLEFINS .5. ADDITION OF N-CHLOROAMIDES TO ENOL ETHERS - SYNTHESIS OF ACYLOXY AND ACYL DERIVATIVES OF ALPHA-AMINO ACETALS AND KETALS (ALDEHYDES AND KETONES) AND OF 2-AMINO SUGARS [J].

DRIGUEZ, H ;

VERMES, JP ;

LESSARD, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (01) :119-130

[7] Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures [J].

Earle, MJ ;

McCormac, PB ;

Seddon, KR .

GREEN CHEMISTRY, 1999, 1 (01) :23-25

[8] TOTAL SYNTHESIS OF ALLOSAMIDIN - AN APPLICATION OF THE SULFONAMIDOGLYCOSYLATION OF GLYCALS [J].

GRIFFITH, DA ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5863-5864

[9] Analysis of the basicity of substituted dimethylamines in different solvents by theoretical descriptors [J].

Headley, AD ;

Nam, J .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (01) :62-68

[10] The effect of the anion on the chemical shifts of the aromatic hydrogen atoms of liquid 1-butyl-3-methylimidazolium salts [J].

Headley, AD ;

Jackson, NM .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (01) :52-55

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