97424-75-4Relevant academic research and scientific papers
B2pin2-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O2 as Oxygen Source and Sole Oxidant
Huang, Jiuzhong,Ouyang, Lu,Li, Jianxiao,Zheng, Jia,Yan, Wuxin,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 5090 - 5093 (2018/09/12)
A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O2) as both the sole oxidant and oxygen source is developed, which was identified by 18O-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation
Wang, Yin,Zhang, Lei,Yang, Yunhui,Zhang, Ping,Du, Zhenting,Wang, Congyang
supporting information, p. 18048 - 18051 (2014/01/06)
Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.
Mechanisms for Manganese(III) Osidations with Alkenes
Fristad, William E.,Peterson, John R.,Ernst, Andreas B.,Urbi, Gordon B.
, p. 3429 - 3442 (2007/10/02)
In the reaction of manganese(III) acetate with carboxylic acids and alkenes, three distinct processes have been identified which involve the alkene and two processes which are independent of alkene.A combination of product studies, rearrangements, dilution experiments and literature kinetic data allow the proposal of a unified mechanistic picture to describe these processes.Specifically, the role of α-H acidity of the carboxylyic acid component, electron deficient radical additions, metal complexed organic radicals, and the importance of an oxo-centered manganese(III) triangle are discussed as they relate to the lactone annulation reaction.Single electron transfer oxidation of alkenes is described as a route toward 1,2-diacetates of alkenes within the 8.1-7.5 eV I.P. range.Three less common modes of Mn(III) reaction are discussed and compared with the two primary processes of lactone annulation and 1,2-diacetate formation.
Electron-transfer Processes: Oxidation of α- and β-Alkenylbenzenes by Peroxydisulphate in Acetic Acid
Citterio, Attilio,Arnoldi, Claudio,Giordano, Claudio,Castaldi, Grasiano
, p. 891 - 896 (2007/10/02)
Oxidation of α- and β-unsaturated alkylbenzenes by peroxydisulphate in acetic acid gives side-chain acetoxylation with formation of the corresponding glycol diacetates and compounds (10), respectively.The reaction is catalysed by transition-metal salts, among which cupric acetate gives the best results.Generally, electron-releasing substituents on the benzene ring increase the yield and improve the selectivity.The same substrates are oxidized in water under Ag+ catalysis to the corresponding aldehydes.The different behaviour in the two solvents is ascribed to the difference in reactivity between the primary oxidation products and the starting olefin, whereas the initial oxidation step is suggested to occur in both cases via an electron-transfer process from the olefin to the sulphate radical anion.
