Organic & Biomolecular Chemistry 2011-03-21

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

Frédéric Louërat, Heather Tye, Spencer Napier, Michael Garrigou, Mark Whittaker, Philippe C Gros

Index: Org. Biomol. Chem. 9(6) , 1768-73, (2011)

Full Text: HTML

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.