Selective aerobic oxidation promoted by highly efficient multi-nitroxy organocatalysts

doi:10.1016/S1872-2067(17)62777-3

Abstract

Abstract:

Selective oxidation with molecular oxygen as the sole oxidant under mild conditions is of crucial importance for the long-term sustainable exploitation of available feedstocks and the formation of required intermediates for organic synthesis and industrial processes. Among the developed oxidation protocols, innovative strategies using hydroxyimide organocatalysts in combination with metallic or metal-free cocatalysts have attracted much attention because of the good activities and selectivities of such catalysts in the oxo functionalization of hydrocarbons. This method is based on the reaction using N-hydroxyphthalimide, which was first reported by Ishii's group in the 1990s. Although the important and wide-ranging applications of such catalysts have been summarized recently, there are no reviews that focus solely on oxidation strategies using multi-nitroxy organocatalysts, which have interesting properties and high reactivities. This review covers the concise synthetic methods and mechanistic profiles of known multi-nitroxy organocatalysts and summarizes significant advances in their use in efficient aerobic oxidation. Based on a combination of experimental and theoretical results, guidelines for the future rational design of multi-nitroxy organocatalysts are proposed, and the properties of various model multi-nitroxy organocatalysts are predicted. The present overview of the advantages, limitations, and potential applications of multi-nitroxy organocatalysts can provide useful tools for researchers in the field of selective oxidation.

Key words: Molecular oxygen, N-hydroxyphthalimide, Organocatalysis, Oxidation, Radical

Kexian Chen, Haiying Xie. Selective aerobic oxidation promoted by highly efficient multi-nitroxy organocatalysts[J]. Chinese Journal of Catalysis, 2017, 38(4): 625-635.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62777-3

https://www.cjcatal.com/EN/Y2017/V38/I4/625

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