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Manganese(IV)‐Mediated Hydroperoxyarylation of Alkenes with Aryl Hydrazines and Dioxygen from Air
Author(s) -
Kindt Stephanie,
Jasch Hannelore,
Heinrich Markus R.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400064
Subject(s) - hydroperoxyl , oxidizing agent , chemistry , manganese , radical , hydrazine (antidepressant) , aryl , oxygen , photochemistry , organic chemistry , inorganic chemistry , alkyl , chromatography
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.