Bronsted acid ionic liquid-catalyzed direct benzylation, allylation and propargylation of 1,3-dicarbonyl compounds with alcohols as well as one-pot synthesis of 4H-chromenes

被引：61

作者：

Funabiki, Kazumasa ^{[1
]}

Komeda, Takuya ^{[1
]}

Kubota, Yasuhiro ^{[1
]}

Matsui, Masaki ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 36期

关键词：

Ionic Bronsted acid catalyst; Substitution; 1,3-Dicarbonyl compounds; Alcohol; NUCLEOPHILIC-SUBSTITUTION; ALKYLATION; DERIVATIVES; BOND;

D O I：

10.1016/j.tet.2009.07.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recyclable ionic Bronsted acid was prepared in nearly quantitative yield by reacting 1-butylimidazole with an equimolar amount of 1,3-propanesultone, followed by treatment with an equimolar amount of trifluoromethanesulfonic acid. The ionic Bronsted acid-catalyzed direct benzylation, allylation and propargylation of 1,3-dicarbonyl compounds with various alcohols in ionic liquid [N-ethyl-N-methyl imidazolium trifluoromethanesulfonate (EMIOTf)], at 100 degrees C for 3 h proceeded smoothly to give the corresponding products in good to excellent yields without the use of any hazardous or volatile solvents and without any by-product such as salts. Furthermore, tandem benzylation-cyclization-dehydration of 1,3-dicarbonyl compounds to give functionalized 4H-chromenes was also achieved in this catalytic reaction. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：7457 / 7463

页数：7

相关论文

共 16 条

[1] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].

Cole, AC ;

Jensen, JL ;

Ntai, I ;

Tran, KLT ;

Weaver, KJ ;

Forbes, DC ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963

[2] A rational approach towards the nucleophilic substitutions of alcohols "on Water" [J].

Cozzi, Pier Giorgio ;

Zoli, Luca .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4162-4166

[3] Facile construction of functionalized 4H-chromene via tandem benzylation and cyclization [J].

Fan, Jinmin ;

Wang, Zhiyong .

CHEMICAL COMMUNICATIONS, 2008, (42) :5381-5383

[4] An efficient Yb(OTf)3 catalyzed alkylation of 1,3-dicarbonyl compounds using alcohols as substrates [J].

Huang, Wen ;

Wang, Jialiang ;

Shen, Quansheng ;

Zhou, Xigeng .

TETRAHEDRON LETTERS, 2007, 48 (23) :3969-3973

[5] A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions [J].

Jana, Umasish ;

Biswas, Srijit ;

Maiti, Sukhendu .

TETRAHEDRON LETTERS, 2007, 48 (23) :4065-4069

[6] FeCl2-Catalyzed selective C-C bond formation by oxidative activation of a benzylic C-H bond [J].

Li, Zhiping ;

Cao, Lin ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6505-6507

[7] Bronsted acid mediated heterogeneous addition reaction of 1,3-dicarbonyl compounds to alkenes and alcohols [J].

Motokura, K ;

Fujita, N ;

Mori, K ;

Mizugaki, T ;

Ebitani, K ;

Kaneda, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2605-2609

[8] Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid bronsted acids [J].

Motokura, Ken ;

Nakagiri, Nobuaki ;

Mizugaki, Tomoo ;

Ebitani, Kohki ;

Kaneda, Kiyotomi .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6006-6015

[9] Highly selective 1,6-addition of aryl boronic acids to α,β,γ,δ-unsaturated carbonyl compounds catalyzed by an iridium complex [J].

Nishimura, Takahiro ;

Yasuhara, Yuichi ;

Hayashi, Tanno .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) :5164-5166

[10] Metal triflate-catalyzed cationic benzylation and allylation of 1,3-dicarbonyl compounds [J].

Noji, Masahiro ;

Konno, Yosuke ;

Ishii, Keitaro .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5161-5167