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Issue 41, 2013
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Recent advances in manganese(iii) acetate mediated organic synthesis

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Abstract

The preceding four decades have witnessed a major expansion in the field of free-radical assisted reactions, as they are becoming a key tool in organic, polymer and complex natural product chemistry. This progress has clearly changed the traditional idea of free-radical reactions being “extremely uncontrollable”, thereby allowing chemists to deal with free radicals in a more accurate and controlled way. Manganese(III) acetate mediated radical reactions have reached distinction in this field, as a wide range of protocols involving manganese(III) acetate under mild and efficient reaction conditions have been developed for the synthesis of biologically active and important organic molecules through oxidation, addition and cyclization reactions, which are in general difficult to achieve by the established synthetic operations. The present review focuses on manganese(III) acetate mediated oxidative free-radical reactions that have been developed and adapted during the last five years. It includes the advancements made in the field of free-radical promoted carbon–carbon and carbon–oxygen bond forming reactions, illustrating the examples of furans, hydrofurans, pyrroles, bicyclic lactones, biaryls, oxepins, indole-alkaloids, 1,2-benzanthracene and C60-fused tetrahydronaphthalene synthesis. Numerous manganese(III) acetate initiated carbon–phosphorus bond formation reactions were also devised during recent years, involving both phosphonyl and phosphinoyl radicals, and are a key part of this review. Manganese(III) acetate promotes functionalization of significant organic compounds, thereby guiding the synthesis of important and complex molecules, such as the formation of propellanes, quinolinones, 1,2-dioxalanes; oxidation of indoles; lactonization of fullerene [C60], malonyl cyclopentanes, glycols; and hydroperoxidation of heterocycles. The review will also envelop several recent milestones that have been achieved in the chemistry of natural products précising the vital role of manganese(III) acetate in the key synthetic steps.

Graphical abstract: Recent advances in manganese(iii) acetate mediated organic synthesis

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Article information


Submitted
20 May 2013
Accepted
23 Jul 2013
First published
25 Jul 2013

RSC Adv., 2013,3, 18716-18754
Article type
Review Article

Recent advances in manganese(III) acetate mediated organic synthesis

M. Mondal and U. Bora, RSC Adv., 2013, 3, 18716
DOI: 10.1039/C3RA42480D

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