Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 35, Pages 7839-7849Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402751
Keywords
Synthetic methods; C-H functionalization; Hydroxylation; Cyclization; Iron
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi
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A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyloxylation of a variety of N,N-disubstituted anilines and N-phenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and o-aminophenols.
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