16735-30-1Relevant academic research and scientific papers
Electrochemically Oxidative α-C-H Functionalization of Ketones: A Cascade Synthesis of α-Amino Ketones Mediated by NH4I
Liang, Sen,Zeng, Cheng-Chu,Tian, Hong-Yu,Sun, Bao-Guo,Luo, Xu-Gang,Ren, Fa-Zheng
, p. 11565 - 11573 (2016)
An efficient electrochemical protocol for the synthesis of α-amino ketones via the oxidative cross-dehydrogenative coupling of ketones and secondary amines has been developed. The electrochemistry performs in a simple undivided cell using NH4I
Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers
Strehl, Julia,Hilt, Gerhard
, p. 5968 - 5972 (2020/08/12)
The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.
Transition-metal-free oxidative α-C-H amination of ketones via a radical mechanism: Mild synthesis of α-amino ketones
Jiang, Qing,Xu, Bin,Zhao, An,Jia, Jing,Liu, Tian,Guo, Cancheng
, p. 8750 - 8756 (2015/01/08)
A transition-metal-free direct α-C.H amination of ketones has been developed using commercially available ammonium iodide as the catalyst and sodium percarbonate as the co-oxidant. A wide range of ketone ((hetero)aromatic or nonaromatic ketones) and amine (primary/secondary amines, anilines, or amides) substrates undergo cross-coupling to generate synthetically useful α-amino ketones. The mechanistic studies indicated that a radical pathway might be involved in the reaction process. The utility of the method is highlighted through a concise one-step synthesis of the pharmaceutical agent amfepramone.
Heteroatom-guided torquoselective olefination of α-oxy and α-amino ketones via ynolates
Shindo, Mitsuru,Yoshikawa, Takashi,Itou, Yasuaki,Mori, Seiji,Nishii, Takeshi,Shishido, Kozo
, p. 524 - 536 (2008/09/20)
Ynolates were found to react with α-alkoxy-, α-siloxy-, and α -aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the β-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms. From experimental and theoretical studies, the high Z selectivity is in duced by orbital and steric interactions rather than by chelation. In a similar manner, α-dialkylamino ketones provided olefins with excellent Z selectivity. These products can be easily converted into multisubstituted butenolides and γ-butyrolactams in good yield.
