Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.
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.
Qin
Hongbo
H
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Yamagiwa
Noriyuki
N
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
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*
D000475:Alkenes; D000577:Amides; D000588:Amines; D002219:Carbamates; D009942:Organometallic Compounds; D013449:Sulfonamides; D000499:Allylamine; D001729:Bismuth