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The Iron‐Catalyzed Oxidation of Alkynes—1,2‐Dione Formation Versus Oxidative Cleavage—A Matter of Temperature
Author(s) -
Enthaler Stephan
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201100206
Subject(s) - chemistry , catalysis , hydrogen peroxide , acetylene , pyridine , oxidative phosphorylation , oxidative cleavage , peroxide , cleavage (geology) , ligand (biochemistry) , medicinal chemistry , catalytic oxidation , photochemistry , organic chemistry , polymer chemistry , materials science , biochemistry , receptor , fracture (geology) , composite material
The iron‐catalyzed oxidation of a variety of alkynes with hydrogen peroxide as the oxidant was examined in detail. Various reaction parameters were investigated in the oxidation of diphenyl acetylene. The best catalytic performance was observed for a combination of FeCl 3 with 4‐dimethylamino pyridine (DMAP) as the ligand, yielding various 1,2‐diones in excellent yields and selectivities at room temperature. Moreover, by subsequently increasing the reaction temperature to 60 °C, a selective oxidative cleavage was observed, resulting in carboxylic acid derivatives.