Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 18, Pages 2929-2939Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600315
Keywords
C-alkylation; allylic alcohols; imidazolium salts; iron(III) catalysts; quinolines
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Funding
- University of Alicante
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Readily available iron(III)-based imidazolium salts have proven to be very versatile catalysts for the allylic substitution reaction of alcohols with anilines, allowing the synthesis of quinolines, 2-allylanilines and 4-allylanilines just by modulating the reaction conditions. Noteworthy, the formation of quinoline derivatives proceeds by ortho-allylation of the corresponding aniline and subsequent oxidative cyclization mediated by atmospheric oxygen. The reaction using anilines as nucleophiles is selective to the C-alkylation versus the N-alkylation, under any reaction conditions studied.
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