477246-90-5Relevant academic research and scientific papers
Exploiting the Nucleophilicity of N-H Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides
Han, Junghoon,Jeon, Mina,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 2769 - 2774 (2016/02/18)
The nucleophilicity of N-unsubstituted imines, which were generated from alkyl azides by a ruthenium-catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N-acylimines, which isomerized to the corresponding e
Protonated aminocyclopentadienyl ruthenium hydride reduction of benzaldehyde and the conversion of the resulting ruthenium triflate to a ruthenium hydride with H2 and base
Casey, Charles P.,Vos, Thomas E.,Singer, Steven W.,Guzei, Ilia A.
, p. 5038 - 5046 (2008/10/08)
Reaction of N-phenyl-2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dienimine (6) with Ru3CO12 formed two isomers of {[2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru (CO)(μ-CO)}2 (8-trans and 8-cis). Photolysis of 8 under a H2 atmosphere led to the formation of the aminocyclopentadienyl ruthenium hydride [2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru( CO)2H (9-H). 9-H reduced benzaldehyde slowly at 75 °C to give benzyl alcohol and 8. Protonation of 9-H with triflic acid produced {[2,5-Me2-3,4-Ph2(η5-C4CNH2 Ph)]Ru(CO)2H}OTf (11-H), which reacted rapidly with benzaldehyde at -80 °C to give benzyl alcohol and [2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru( CO)2OTf (9-OTf). Reaction of 9-OTf with H2 and base led to the re-formation of 9-H. These reactions provide the transformations required for a catalytic cycle for hydrogenation of aldehydes.
