Issue 6, 2011
From the journal:

Organic & Biomolecular Chemistry

TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds†‡

Frédéric Louërat,a   Heather Tye,b   Spencer Napier,b   Michael Garrigou,b   Mark Whittakerb  and  Philippe C. Gros*a  

* Corresponding authors

a Groupe SOR, SRSMC, CNRS, Nancy Université, Boulevard des Aiguillettes, Vandoeuvre-Lès-Nancy, France
E-mail: philippe.gros@srsmc.uhp-nancy.fr
Fax: +33 38368 4785
Tel: +33 38368 4979

b Evotec (UK) Ltd, 114 Milton Park, Abingdon, Oxfordshire, UK

Abstract

The concomitant use of silver oxide and catalytic amount of TBAF allowed the efficient and chemoselective coupling of readily available 4-chloro- and 4-methyl-2-trimethyl-silyl-pyridines with heteroaromatic and aromatic halides. Based on control experiments, a mechanism involving the formation of a pyridylsilver intermediate and TBAF recycling is postulated.

Graphical abstract: TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds

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Article information

DOI
https://doi.org/10.1039/C0OB00710B
Article type
Paper
Submitted
13 Sep 2010
Accepted
09 Dec 2010
First published
24 Jan 2011

Org. Biomol. Chem., 2011,9, 1768-1773

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TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds

F. Louërat, H. Tye, S. Napier, M. Garrigou, M. Whittaker and P. C. Gros, Org. Biomol. Chem., 2011, 9, 1768 DOI: 10.1039/C0OB00710B

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