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Synthesis 2011(22): 3604-3611  
DOI: 10.1055/s-0030-1260256
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© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

Sébastien Ladouceur, Ahmed M. Soliman, Eli Zysman-Colman*
Département de chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, Québec, J1K 2R1, Canada
Fax: +1(819)8218017; e-Mail: Eli.Zysman-Colman@usherbrooke.ca;
Further Information

Publication History

Received 11 August 2011
Publication Date:
06 October 2011 (online)

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Abstract

1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

Key words

click chemistry - Huisgen cycloaddition - triazoles - alkynes - azides

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16

Control reactions with 1g demonstrated the following: In the absence of pyridine, after 24 hours only a 20% deprotection was observed with a corresponding 20% conversion into 2g, as determined by GC-MS. In the absence of K2CO3, deprotection of 1g was completely arrested.