109462-13-7Relevant academic research and scientific papers
Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations
Zhu, Qilei,Gentry, Emily C.,Knowles, Robert R.
supporting information, p. 9969 - 9973 (2016/08/16)
A new catalytic method is described to access carbocation intermediates via the mesolytic cleavage of alkoxyamine radical cations. In this process, electron transfer between an excited state oxidant and a TEMPO-derived alkoxyamine substrate gives rise to a radical cation with a remarkably weak C?O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO.as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic partners.
Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope
Sasano, Yusuke,Kogure, Naoki,Nishiyama, Tomohiro,Nagasawa, Shota,Iwabuchi, Yoshiharu
, p. 1004 - 1009 (2015/03/31)
The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.
SYNTHETIC STUDIES OF MARINE ALKALOIDS HAPALINDOLES. Part 1. TOTAL SYNTHESIS OF (+/-)-HAPALINDOLES J and M
Muratake, Hideaki,Natsume, Mitsutaka
, p. 6331 - 6342 (2007/10/02)
The first concise synthesis of marine indole alkaloids (+/-) hapalindoles J (4) and M (5) was achieved in seven or six steps starting from a readily available compound 6 using important key reactions, 6 -> 7 -> 8 and 35 -> 41 or 5.
