SRN1 REACTIONS OF CHLOROTRIFLUOROMETHYL PYRIDINES WITH NAPHTHOLATE, PHENOLATE AND MALONATE ANIONS

2-Chloropyridines, bearing a CF3 group on position 3,4, 5 or 6 (2-Cl Py 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 generated 2-pyridyl radical and the carbanionic site of the nucleophile yields 2-heterobiaryl derivatives (CF3Py-Nap-OH or CF3Py-PhOH). Similarly, coupling of the 2-amino-5-CF3-3-pyridyl radical yields 3-heterobiaryl derivatives. Coupling of the malonate anion takes place with the aforementioned radicals.