Catalyst-Controlled Highly Selective Coupling and Oxygenation of Olefins: A Direct Approach to Alcohols, Ketones, and Diketones
作者:Yijin Su、Xiang Sun、Guolin Wu、Ning Jiao
DOI:10.1002/anie.201303917
日期:2013.9.9
Oxygen? That's radical! A method for the direct synthesis of substituted alcohols, ketones, and diketones through a catalyst‐controlled highly chemoselective coupling and oxygenation of olefins has been developed. The method is simple and practical, can be switched by the selection of different catalysts, and employs molecular oxygen as both an oxidant and a reagent.
Herein, we disclose a strategy for the activation of N‐(acyloxy)phthalimides towards photoinducedelectrontransfer through hydrogen bonding. This activation mode enables efficient access to C(sp3)‐centered radicals upon decarboxylation from bench‐stable and readily available substrates. Moreover, we demonstrate that the formed alkyl radicals can be successfully employed in a novel redox‐neutral method
A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassiumferrocyanidetrihydrate (K4[Fe(CN)6]⋅3 H2O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions