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. 2006 Feb 8;128(5):1611-4.
doi: 10.1021/ja056112d.

Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides

Hongbo Qin  1 , Noriyuki Yamagiwa, Shigeki Matsunaga, Masakatsu Shibasaki
Affiliations

Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides

Hongbo Qin et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc. 2006 Mar 29;128(12):4162

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.

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