Indium(III) bromide catalyzed rapid propargylation of heteroaromatic systems by α-aryl-substituted propargyl alcohols

Yadav, J. S. ; Subba Reddy, B. V. ; Raghavendra Rao, K. V. ; Narayana Kumar, G. G. K. S. (2007) Indium(III) bromide catalyzed rapid propargylation of heteroaromatic systems by α-aryl-substituted propargyl alcohols Synthesis, 2007 (20). pp. 3205-3210. ISSN 0039-7881

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Official URL: http://www.thieme-connect.com/ejournals/abstract/s...

Related URL: http://dx.doi.org/10.1055/s-2007-990797

Abstract

A variety of heteroaromatic compounds such as indole, carbazole, pyrrole, and furan underwent smooth coupling with propargylic alcohols in the presence of 10 mol% of indium(III) bromide under mild conditions to furnish exclusively propargylated heterocycles in excellent yields and high regioselectivity. The use of indium(III) bromide makes this procedure simple, convenient, and practical. The hydroxy groups of the propargylic alcohols were simply replaced by the nucleophiles in an SN2' manner.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Indium Reagents; Nucleophilic Substitution; C-alkylation; Propargylation
ID Code:63127
Deposited On:28 Sep 2011 03:34
Last Modified:28 Sep 2011 03:34

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