N,N-Chelate-control on the regioselectivity in acetate-assisted C–H activation

Warren B. Cross; Eric G. Hope; Yi-Hsien Lin; Stuart A. Macgregor; Kuldip Singh; Gregory A. Solan; Nurhusna Yahya

doi:10.1039/C3CC38697J

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Chemical Communications

Issue 19, 2013

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N,N-Chelate-control on the regioselectivity in acetate-assisted C–H activation

Warren B. Cross,^a Eric G. Hope,^a Yi-Hsien Lin,^a Stuart A. Macgregor,^b Kuldip Singh,^a Gregory A. Solan*^a and Nurhusna Yahya^a

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Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK
E-mail: gas8@leicester.ac.uk ;
Fax: +44-116-252-3789 ;
Tel: +44-116-252-2096

Institute of Chemical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, UK

Chem. Commun., 2013,49, 1918-1920

DOI: 10.1039/C3CC38697J
Received 04 Dec 2012, Accepted 18 Jan 2013
First published online 21 Jan 2013

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Bidentate N,N-pyridylimine or N,N-pyridylamine donors are effective chelating ligands for regiospecific C–H activation at the peri-(C₈)-position of a naphthyl ring on reaction with palladium(II) acetate; DFT calculations show N,N-chelates bias the cyclopalladation towards 6-membered ring products.

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Warren B. Cross
Eric G. Hope
Yi-Hsien Lin
Stuart A. Macgregor
Kuldip Singh
Gregory A. Solan
Nurhusna Yahya

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