Paper
Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.
Published Jan 17, 2006 · Hong-Bo Qin, Noriyuki Yamagiwa, S. Matsunaga
Journal of the American Chemical Society
109
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0
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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.
Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides efficiently produces allylic amines in good yield (up to 96%) within 24 hours at 25-100 degrees C in 1,4
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