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 pyridylsilver intermediate and TBAF recycling is postulated.
Groupe SOR, SRSMC, CNRS, Nancy Université, Boulevard des Aiguillettes, 54506, Vandoeuvre-Lès-Nancy, France.
Frédéric
F
Louërat
Heather
H
Tye
Spencer
S
Napier
Michael
M
Garrigou
Mark
M
Whittaker
Philippe C
PC
Gros
D000498:Allyl Compounds / Q000737:chemistry; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D003432:Cross-Linking Reagents; D010087:Oxides; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; D018030:Silver Compounds; C040225:disilver oxide; C009405:tetrabutylammonium; C023666:pyridine