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

Thomas Storr; Christopher Teskey; Michael Greaney

doi:10.1002/chem.201603783

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

Thomas Storr, Christopher Teskey, Michael Greaney

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Abstract

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.

Original language	English
Pages (from-to)	18169-18178
Journal	Chem.Eur. J.
Volume	22
Issue number	50
Early online date	7 Nov 2016
DOIs	https://doi.org/10.1002/chem.201603783
Publication status	Published - 12 Dec 2016

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abstract = "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.",

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AU - Teskey, Christopher

AU - Greaney, Michael

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N2 - 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.

AB - 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.

U2 - 10.1002/chem.201603783

DO - 10.1002/chem.201603783

M3 - Article

SN - 0947-6539

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SP - 18169

EP - 18178

JO - Chem.Eur. J.

JF - Chem.Eur. J.

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ER -

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

Abstract

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