Manganese(IV)-mediated hydroperoxyarylation of alkenes with aryl hydrazines and dioxygen from air.

Stephanie Kindt, Hannelore Jasch, Markus R Heinrich

Chemistry (Weinheim an der Bergstrasse, Germany) 2014 May 19

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We report a new carbooxygenation-type version of the Meerwein arylation in which the introduction of oxygen is achieved by using dioxygen from the air. In this way, hydroperoxides were obtained from activated as well as non-activated alkenes by oxidizing aryl hydrazines with manganese dioxide. The best results were obtained with α-substituted acrylates. Importantly, the aryl hydrazine has to be added slowly to the reaction mixture to allow sufficient uptake of dioxygen from the air. Competition and labeling experiments revealed hydroperoxyl radicals as novel oxygen-centered radical scavengers. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Stephanie Kindt, Hannelore Jasch, Markus R Heinrich. Manganese(IV)-mediated hydroperoxyarylation of alkenes with aryl hydrazines and dioxygen from air. Chemistry (Weinheim an der Bergstrasse, Germany). 2014 May 19;20(21):6251-5