Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes

Thomas E. Storr; Christopher J. Teskey; Michael F. Greaney

doi:10.1002/chem.201603783

Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes

Thomas E. Storr, Christopher J. Teskey, Michael F. Greaney

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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
Number of pages	10
Journal	Chemistry - A European Journal
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

Keywords

C−H activation
cross-dehydrogenative-coupling
diarylmethane
homogeneous catalysis
tandem reactions

Access to Document

10.1002/chem.201603783

http://doi.wiley.com/10.1002/chem.201603783

Cite this

@article{d87465d1244e418ab7218fb47a75acdf,

title = "Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes",

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.",

keywords = "C−H activation, cross-dehydrogenative-coupling, diarylmethane, homogeneous catalysis, tandem reactions",

author = "Storr, {Thomas E.} and Teskey, {Christopher J.} and Greaney, {Michael F.}",

year = "2016",

month = dec,

day = "12",

doi = "10.1002/chem.201603783",

language = "English",

volume = "22",

pages = "18169--18178",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley",

number = "50",

}

TY - JOUR

T1 - Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes

AU - Storr, Thomas E.

AU - Teskey, Christopher J.

AU - Greaney, Michael F.

PY - 2016/12/12

Y1 - 2016/12/12

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.

KW - C−H activation

KW - cross-dehydrogenative-coupling

KW - diarylmethane

KW - homogeneous catalysis

KW - tandem reactions

UR - https://www.research.manchester.ac.uk/portal/en/publications/the-crossdehydrogenativecoupling-of-alkoxybenzenes-with-toluenes-copperii-halide-mediated-tandem-halobenzylation-of-arenes(55e7e0f2-5576-4d87-bf98-4c40613670c4)/export.html

U2 - 10.1002/chem.201603783

DO - 10.1002/chem.201603783

M3 - Article

VL - 22

SP - 18169

EP - 18178

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 50

ER -

Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes

Abstract

Keywords

Access to Document

Other files and links

Thomas Storr

Cite this

Cross-dehydrogenative-coupling of alkoxybenzenes with toluenes: Copper(II) halide mediated tandem halo/benzylation of arenes

Abstract

Keywords

Access to Document

Other files and links

Profiles

Thomas Storr

Cite this