title: Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.
abstract: A Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system efficiently promoted intermolecular 1:1 hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides to afford allylic amines in good yield (up to 96%). Reaction proceeded with 0.5-10 mol % catalyst loading at 25-100 degrees C (generally at 50 degrees C) in 1,4-dioxane within 24 h. The Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system constitutes a new entry into series of intermolecular hydroamination catalysis. Mechanistic studies and the postulated reaction mechanism are also discussed.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Hongbo
authors.initials: H
authors.lastname: Qin
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Yamagiwa
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000499:Allylamine / Q000138:chemical synthesis; D000577:Amides / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000138:chemical synthesis*; D001729:Bismuth / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000577:Amides; D000588:Amines; D002219:Carbamates; D009942:Organometallic Compounds; D013449:Sulfonamides; D000499:Allylamine; D001729:Bismuth