title: Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines.
abstract: 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.
authors.affiliation: Inorganic & Physical Chemistry Division, Indian Institute of Chemical Technology (Council of Scientific & Industrial Research), Hyderabad-500607, India. sreedharb@iict.res.in.
authors.forename: Vikas S
authors.initials: VS
authors.lastname: Rawat
authors.forename: Thulasiram
authors.initials: T
authors.lastname: Bathini
authors.forename: S
authors.initials: S
authors.lastname: Govardan
authors.forename: Bojja
authors.initials: B
authors.lastname: Sreedhar
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002082:Butylamines / Q000737:chemistry; D055772:Green Chemistry Technology; D008752:Methylene Chloride / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010880:Piperidines / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000737:chemistry
chemical_list: D000480:Alkynes; D002082:Butylamines; D010880:Piperidines; D011437:Propylamines; D011759:Pyrrolidines; C009054:propargylamine; D008752:Methylene Chloride; D010293:Pargyline