☆ 4.4 Article

Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel-Crafts amidoalkylation of indoles with aryl aldimines

TETRAHEDRON LETTERS (2011)

Journal

TETRAHEDRON LETTERS

Volume 52, Issue 36, Pages 4671-4674

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tetlet.2011.07.010

Keywords

Hydrogen phosphites; Hydrogen phosphates; Indoles; Friedel-Crafts; Amidoalkylation

Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China [21072145]
Foundation for the Author of National Excellent Doctoral Dissertation of PR China [200931]
Natural Science Foundation of Jiangsu Province of China [BK2009115]

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Abstract

A highly efficient and selective Friedel-Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel-Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

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