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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;
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Recently, a catalytic oxidation of saturated ketones into α,β-unsaturated ketones has been achieved by a hypervalent iodine, see
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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.
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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;
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70349960732
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See the Supporting Information
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See the Supporting Information.
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25
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70349940393
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3-Pentanone and 3-dodecanone were transformed into the corresponding products in 34% and 31% yields, respectively.
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3-Pentanone and 3-dodecanone were transformed into the corresponding products in 34% and 31% yields, respectively.
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27
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b) J. Cámpora. C. M. Maya, P. Palma, E. Carmona, E. Gutierrez-Puebla, C. Ruiz, J. Am. Chem. Soc. 2003, 125, 1482.
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28
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70349949748
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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.
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