Ruthenium-Catalyzed Oxidative Cyanation of Tertiary Amines with Molecular Oxygen or Hydrogen Peroxide and Sodium Cyanide: sp3 C− H Bond Activation and …

SI Murahashi, T Nakae, H Terai…

Index: Murahashi, Shun-Ichi; Nakae, Takahiro; Terai, Hiroyuki; Komiya, Naruyoshi Journal of the American Chemical Society, 2008 , vol. 130, # 33 p. 11005 - 11012

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Citation Number: 246

Abstract

Ruthenium-catalyzed oxidative cyanation of tertiary amines with molecular oxygen in the presence of sodium cyanide and acetic acid gives the corresponding α-aminonitriles, which are highly useful intermediates for organic synthesis. The reaction is the first demonstration of direct sp3 C− H bond activation α to nitrogen followed by carbon− carbon bond formation under aerobic oxidation conditions. The catalytic oxidation seems to proceed by (i) α-C− H ...