An FeCl3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols

被引：134

作者：

Jana, Umasish ^{[1
]}

Maiti, Sukhendu ^{[1
]}

Biswas, Srijit ^{[1
]}

机构：

[1] Jadavpur Univ, Dept Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 40期

关键词：

indole; ferric chloride; alkylation; alcohols; atom-economical;

D O I：

10.1016/j.tetlet.2007.07.208

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The FeCl3-catalyzed C3-selective Friedel-Crafts alkylation of indoles using allylic, benzylic and propargylic alcohols has been developed. The reaction was performed in the presence of a catalytic amount of inexpensive anhydrous FeCl3 (10 mol %) in nitromethane under mild conditions. This method can also be used for the alkylation of pyrrole. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7160 / 7163

页数：4

相关论文

共 14 条

[1] Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols [J].

Inada, Y ;

Yoshikawa, M ;

Milton, MD ;

Nishibayashi, Y ;

Uemura, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (04) :881-890

[2] 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

[3]

Joule J.A., 2000, HETEROCYCLIC CHEM, V4th

[4] Rhenium-catalyzed aromatic propargylation [J].

Kennedy-Smith, JJ ;

Young, LA ;

Toste, FD .

ORGANIC LETTERS, 2004, 6 (08) :1325-1327

[5]

Kimura M, 2006, HETEROCYCLES, V67, P535

[6] Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane [J].

Kimura, M ;

Futamata, M ;

Mukai, R ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4592-4593

[7] Palladium-catalyzed functionalization of indoles with 2-acetoxymethyl-substituted electron-deficient alkenes [J].

Ma, Shengming ;

Yu, Shichao ;

Peng, Zhihua ;

Guo, Hao .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) :9865-9868

[8] Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols [J].

Nishibayashi, Y ;

Yoshikawa, M ;

Inada, Y ;

Hidai, M ;

Uemura, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11846-11847

[9]

Sundberg R.J., 1996, INDOLES

[10] THE ATOM ECONOMY - A SEARCH FOR SYNTHETIC EFFICIENCY [J].

TROST, BM .

SCIENCE, 1991, 254 (5037) :1471-1477