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 |
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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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