Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 9, Pages 1390-1397Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200801222
Keywords
Fluorine; Sulfur heterocycles; Synthetic methods; Electrophilic trifluoromethylation; Halogenation; Multicomponent reactions
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Funding
- GlaxoSmithKline
- CNRS
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Here we describe work devoted to the one-pot preparation of electrophilic trifluoromethylating reagents. The first part describes a reappraisal of our earlier experimental conditions and leads to an improved protocol that avoids the use of solvent and allows better yields. The second part carefully studies the behavior of biaryl substrates, whose structures can drive the reaction through the formation of original noncyclic or tricyclic dibenzothiophenium salts. New compounds were tested, in a standard reaction with aniline, for their trifluoromethylating power and revealed equivalent or improved reactivity relative to that of existing reagents. Furthermore, contrary to common knowledge, the presence of electron-donating methyl groups gave reagents with very high activity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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