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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-03, Vol.9 (6), p.1768-1773
Main Authors: Louërat, Frédéric, Tye, Heather, Napier, Spencer, Garrigou, Michael, Whittaker, Mark, Gros, Philippe C
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
Catalysis
Cross-Linking Reagents - chemistry
Molecular Structure
Oxides - chemistry
Pyridines - chemistry
Quaternary Ammonium Compounds - chemistry
Silver Compounds - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00710b