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Volumn 48, Issue 25, 2009, Pages 4543-4545

Nickel-catalyzed formation of a carbon-nitrogen bond at the β position of saturated ketones

Author keywords

enaminones; Amination; Ketones; Nickel catalysis; Oxidation

Indexed keywords

A-CARBON; ENAMINONES; ETHYL KETONES; MORPHOLINES; NICKEL CATALYSIS; NITROGEN BONDS; PROPIOPHENONE; SECONDARY AMINES;

EID: 70349964335     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900892     Document Type: Article
Times cited : (88)

References (31)
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    • For representative reviews, see: a) L. Pu, H. B. Yu, Chem. Rev. 2001, 101, 757;
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    • For representative reviews, see: a) L. M. Jackman, B. C. Lange, Tetrahedron 1977, 33, 2737;
    • (1977) Tetrahedron , vol.33 , pp. 2737
    • Jackman, L.M.1    Lange, B.C.2
  • 9
    • 33947644069 scopus 로고    scopus 로고
    • β functionalization of carboxylic acid derivatives utilizing directing groups have been reported: a R. Giri, N. Maugel. J. J. Li, D. H. Wang, S. P. Breazzano. L. B. Saunders. J.-Q. Yu, J. Am. Chem. Soc. 2007, 129.3510;
    • β functionalization of carboxylic acid derivatives utilizing directing groups have been reported: a) R. Giri, N. Maugel. J. J. Li, D. H. Wang, S. P. Breazzano. L. B. Saunders. J.-Q. Yu, J. Am. Chem. Soc. 2007, 129.3510;
  • 11
    • 0026785465 scopus 로고
    • Palladium-catalyzed oxidative amination of α,β-unsaturated carbonyl compounds are known, see: a
    • Palladium-catalyzed oxidative amination of α,β-unsaturated carbonyl compounds are known, see: a) T. Hosokawa, M. Takano, Y. Kuroki, S.-I. Murahashi. Tetrahedron Lett. 1992, 33, 6643:
    • (1992) Tetrahedron Lett , vol.33 , Issue.6643
    • Hosokawa, T.1    Takano, M.2    Kuroki, Y.3    Murahashi, S.-I.4
  • 13
    • 34047161855 scopus 로고    scopus 로고
    • For palladium-catalyzed aza-Wacker reactions, see
    • For palladium-catalyzed aza-Wacker reactions, see: V. Kotov, C. C. Scarborough, S. S. Stahl, Inorg. Chem. 2007, 46, 1910.
    • (2007) Inorg. Chem , vol.46 , pp. 1910
    • Kotov, V.1    Scarborough, C.C.2    Stahl, S.S.3
  • 18
    • 67749120518 scopus 로고    scopus 로고
    • Recently, a catalytic oxidation of saturated ketones into α,β-unsaturated ketones has been achieved by a hypervalent iodine, see
    • Recently, a catalytic oxidation of saturated ketones into α,β-unsaturated ketones has been achieved by a hypervalent iodine, see: M. Uyanik, M. Akakura, K. Ishihara, J. Am. Chem. Soc. 2009, 131, 251.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 251
    • Uyanik, M.1    Akakura, M.2    Ishihara, K.3
  • 21
    • 0037051609 scopus 로고    scopus 로고
    • In the nickel-catalyzed α-arylation of ketones, bisphosphane ligands were used to avoid α-hydride elimination, see: a D.J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500;
    • In the nickel-catalyzed α-arylation of ketones, bisphosphane ligands were used to avoid α-hydride elimination, see: a) D.J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500;
  • 24
    • 70349960732 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 25
    • 70349940393 scopus 로고    scopus 로고
    • 3-Pentanone and 3-dodecanone were transformed into the corresponding products in 34% and 31% yields, respectively.
    • 3-Pentanone and 3-dodecanone were transformed into the corresponding products in 34% and 31% yields, respectively.
  • 28
    • 70349949748 scopus 로고    scopus 로고
    • Consistent with the mechanism in Scheme 1 was the formation of naphthalene in the following experiment by using 1-chloronaphthalene in place of chlorobenzene. When a mixture of 1a (0.51 mmol). 2a, and the nickel catalyst was treated with 1-chloronaphthalene (2.0 mmol) at 100°C for 40 hours, naphthalene (0.84 mmol) and 3a (0.42 mmol) were obtained from the resulting mixture.
    • Consistent with the mechanism in Scheme 1 was the formation of naphthalene in the following experiment by using 1-chloronaphthalene in place of chlorobenzene. When a mixture of 1a (0.51 mmol). 2a, and the nickel catalyst was treated with 1-chloronaphthalene (2.0 mmol) at 100°C for 40 hours, naphthalene (0.84 mmol) and 3a (0.42 mmol) were obtained from the resulting mixture.
  • 30


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