Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines

Propargylamines are synthesized via metal-free activation of the C-halogen bond of dihalomethanes and the C-H bond of terminal alkynes in a three-component coupling without catalyst or additional base and under mild reaction conditions. The dihalomethanes are used both as solvents as well as precurs...

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Veröffentlicht in:Organic & biomolecular chemistry 2014-09, Vol.12 (34), p.6725-6729
Hauptverfasser: Rawat, Vikas S, Bathini, Thulasiram, Govardan, S, Sreedhar, Bojja
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container_end_page 6729
container_issue 34
container_start_page 6725
container_title Organic & biomolecular chemistry
container_volume 12
creator Rawat, Vikas S
Bathini, Thulasiram
Govardan, S
Sreedhar, Bojja
description Propargylamines are synthesized via metal-free activation of the C-halogen bond of dihalomethanes and the C-H bond of terminal alkynes in a three-component coupling without catalyst or additional base and under mild reaction conditions. The dihalomethanes are used both as solvents as well as precursors for the methylene fragment (C1) in the final product. The scope of the reaction and the influence of various reaction variables has been investigated. A plausible reaction mechanism is proposed and the involvement of various intermediates that can be generated in situ in the process is discussed. The metal-free conditions also make this protocol environmentally benign and atom economical.
doi_str_mv 10.1039/c4ob00986j
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Alkynes - chemistry
Butylamines - chemistry
Green Chemistry Technology
Methylene Chloride - chemistry
Molecular Structure
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
Piperidines - chemistry
Propylamines - chemical synthesis
Pyrrolidines - chemistry
title Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines
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