R. Beugelmans, J. Chastanet
Sep 3, 1993
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract - 2-Chloropyridines, bearing a CF 3 group on position 3, 4, 5 or 6 (2-Cl Py CF 3 ) were found to be suitable substrates for photostimulated S RN 1 reactions with nucleophiles derived from 2-naphthol (Nap-OH) or from phenol (PhOH). Carbon-carbon coupling between the regiospecifically generated 2-pyridyl radical and the carbanionic site of the nucleophile yields 2-heterobiaryl derivatives (CF 3 Py-Nap-OH or CF 3 Py-PhOH). Similarly, coupling of the 2-amino-5-CF 3- 3-pyridyl radical yields 3-heterobiaryl derivatives. Coupling of the malonate anion takes place with the aforementioned radicals.