R. Beugelmans et J. Chastanet, SRN1 REACTIONS OF CHLOROTRIFLUOROMETHYL PYRIDINES WITH NAPHTHOLATE, PHENOLATE AND MALONATE ANIONS, Tetrahedron, 49(36), 1993, pp. 7883-7890
2-Chloropyridines, bearing a CF3 group on position 3,4, 5 or 6 (2-Cl P
y CF3) were found to be suitable substrates for photostimulated S(RN)1
''actions with nucleophiles derived from 2-naphthol (Nap-OH) or from
phenol (PhOH). Carbon-carbon coupling between the regiospecifically ge
nerated 2-pyridyl radical and the carbanionic site of the nucleophile
yields 2-heterobiaryl derivatives (CF3Py-Nap-OH or CF3Py-PhOH). Simila
rly, coupling of the 2-amino-5-CF3-3-pyridyl radical yields 3-heterobi
aryl derivatives. Coupling of the malonate anion takes place with the
aforementioned radicals.