Cross-Dehydrogenative-Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes

A cross‐dehydrogenative‐coupling of alkoxybenzenes and toluenes with concomitant halogenation is reported. Conditions employed were the use of stoichiometric copper halide salts and dialkylperoxides to afford a range of bromoalkoxydi‐ and triarylmethanes. Preliminary mechanistic studies suggest that...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-12, Vol.22 (50), p.18169-18178
Main Authors: Storr, Thomas E., Teskey, Christopher J., Greaney, Michael F.
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemistry
Copper
Coupling
cross-dehydrogenative-coupling
C−H activation
diarylmethane
Halides
Halogenation
Halos
homogeneous catalysis
Radicals
Synthesis
tandem reactions
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Summary:A cross‐dehydrogenative‐coupling of alkoxybenzenes and toluenes with concomitant halogenation is reported. Conditions employed were the use of stoichiometric copper halide salts and dialkylperoxides to afford a range of bromoalkoxydi‐ and triarylmethanes. Preliminary mechanistic studies suggest that the in situ production of haloarenes (or dihaloarenes) followed by a copper‐mediated coupling of a benzylic radical is operational. Two steps away: A copper‐mediated cross‐dehydrogenative‐coupling of alkoxybenzenes and toluenes with concomitant halogenation is reported (see figure). A range of bromoalkoxydi‐ and triarylmethanes are synthesized and a plausible mechanism is proposed.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201603783