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A Mild Oxidative Aryl Radical Addition into Alkenes by Aerobic Oxidation of Arylhydrazines
Author(s) -
Taniguchi Tsuyoshi,
Zaimoku Hisaaki,
Ishibashi Hiroyuki
Publication year - 2011
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.201003060
Subject(s) - chemistry , catalysis , aniline , hydrazine (antidepressant) , radical , aryl , radical initiator , potassium ferrocyanide , oxygen , oxidative phosphorylation , photochemistry , organic chemistry , polymerization , biochemistry , alkyl , chromatography , polymer
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 potassium ferrocyanide trihydrate (K 4 [Fe(CN) 6 ]⋅3 H 2 O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions were achieved at room temperature in the presence of iron catalyst, oxygen gas, and water. A method involving aniline as a radical precursor is also described.