89787-34-8Relevant academic research and scientific papers
Cu-catalyzed sequential dehydrogenation-conjugate addition for β-functionalization of saturated ketones: Scope and mechanism
Jie, Xiaoming,Shang, Yaping,Zhang, Xiaofeng,Su, Weiping
supporting information, p. 5623 - 5633 (2016/05/24)
The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.
Electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether. Effect of the substituent on the formation of Mannich bases. II.
Renaud, Roger N.,Stephens, Campbell J.,Brochu, Gaetan
, p. 565 - 569 (2007/10/02)
The formation of Mannich bases from the electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether was studied.The yield of bases obtained depended on the relative oxidation potentials of the starting amine compound and the base formed.An electron-donating substituent on the amine showed a large difference in the oxidation potentials and gave the highest yield of product.On the other hand, the oxidation potentials were very close with an electron-withdrawing substituent and the yield in base was relatively much lower.Furthermore, the main product in the case of an electron-withdrawing group in the presence of 1-trimethylsilyloxy-1-cyclohexene was 4-substituted 2-(2-oxocyclohexyl)-N,N-dimethylaniline.Some side products were also isolated and were identified as N,N-diketonic compounds.
