75490-55-0Relevant academic research and scientific papers
Copper-Catalyzed Oxidative Coupling of AIBN and Ketone-Derived Enoxysilanes to γ-Ketonitriles
Zhang, Xuexia,Huang, Hanmin
, p. 4998 - 5001 (2018)
A new and efficient oxidative coupling reaction between enoxysilane and alkylnitrile radicals derived from readily available AIBN and its analogues has been developed by using redox-active metal as a catalyst in which the redox-active copper is used for enhancing the electrophilicity of a free radical via coordination and bringing the radical and nucleophilic enol ether closer to facilitate the single-electron transfer. The present catalytic protocol afforded a variety of γ-ketonitriles in good to excellent yields with good functional group tolerance.
Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis
Cao, Haoying,Ma, Shanshan,Feng, Yanhong,Guo, Yawen,Jiao, Peng
supporting information, p. 1780 - 1783 (2022/02/17)
Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.
Unactivated C(sp3)-H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies
Lan, Xing-Wang,Wang, Nai-Xing,Bai, Cui-Bing,Lan, Cui-Lan,Zhang, Tong,Chen, Shi-Lu,Xing, Yalan
supporting information, p. 5986 - 5989 (2016/12/09)
The first example of a metal-free unactivated C(sp3)-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)-H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway.
