Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylaminesElectronic supplementary information (ESI) available: FTIR, 1H NMR, 13C NMR, LRMS and HRMS data, and 1H and 13C NMR spectra. See DOI: 10.1039/c4ob00986j

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 (C 1 ) 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. 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.