98750-17-5Relevant academic research and scientific papers
PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones
Chen, Ming,Zhang, Wei,Ren, Zhi-Hui,Gao, Wen-Yun,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 761 - 768 (2017/06/05)
Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.
Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process
Zhou, Xiaoqiang,Ma, Haojie,Cao, Jinhui,Liu, Xingxing,Huang, Guosheng
supporting information, p. 10070 - 10073 (2016/11/06)
Hydrogen peroxide and anhydride mediated transformation of enamides to afford substituted α-acyloxy ketones is described. This transition-metal-free cascade reaction has a broad substrate scope and high efficiency. The acyl intramolecular migration procedure successfully achieved this acyloxylation process under mild conditions and increased the atom efficiency.
Straightforward and highly efficient synthesis of α-acetoxy ketones through gold-catalyzed intermolecular oxidation of terminal alkynes
Wu, Chao,Liang, Zhiwu,Yan, Dong,He, Weimin,Xiang, Jiannan
, p. 2605 - 2611 (2013/09/24)
A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O-H insertion.
The reaction of terminal alkynes with PhI(OAc)2: a convenient procedure for the preparation of α-acyloxy ketones
Mo, Dong-Liang,Dai, Li-Xin,Hou, Xue-Long
supporting information; experimental part, p. 5578 - 5581 (2011/02/22)
Treatment of terminal alkynes with PhI(OAc)2 in different acids at 70 °C provided the corresponding α-acyloxy ketones in good to excellent yields. A plausible mechanism has been proposed based on the experimental results.
Radical-Cations as Intermediates in the Oxidation of Alkenes by Metal Ions
Norman, Julie A.,Thomas, C. Barry,Burrow, Michael J.
, p. 1087 - 1094 (2007/10/02)
The formation of hydroxy acetates in the reaction of some alkenes with lead(IV), cobalt(III), and manganese(III) in acetic acid is demonstrated to involve the intermediacy of alkene radical-cations.A study employing a range of aryl-substituted alkenes has shown that there is an inverse relationship between the yield of hydroxy acetate and the ionisation potential of the organic substrate.The electron deficiency in the radical-cations derived from these alkenes appears to be localised on the double bond: no evidence could be obtained for reaction at the aromatic ring.The introduction of the chlorine atom into this ring had the effect of repressing electron-transfer in cobalt(III) and manganese(III) oxidations but not in those involving lead(IV).
