title: Synthesis of α-tribromomethylamines via Mg-mediated addition of bromoform to imines.
abstract: Mg-mediated addition of bromoform to electron deficient imines such as N-sulfonylimines affords α-tribromomethylated N-sulfonylamines in good to excellent yields. The procedure could be further simplified by transforming the imine precursors, α-sulfonyl-N-tosyl- and Boc-amines, in one pot to the corresponding α-tribromomethyl derivatives. Facile removal of the Boc protecting group in nearly quantitative yield and a silver carbonate mediated monodebromination have also been demonstrated.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India. irishi@iitb.ac.in.
authors.forename: Elumalai
authors.initials: E
authors.lastname: Gopi
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D002384:Catalysis; D004583:Electrons; D007097:Imines / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D008744:Methylamines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D022882:Trihalomethanes / Q000737:chemistry
chemical_list: D007097:Imines; D008744:Methylamines; D022882:Trihalomethanes; D008274:Magnesium; C015044:bromoform