S(RN)1 reactions of chlorotrifluoromethyl pyridines with naphtholate, phenolate and malonate anions

Article abstract of DOI:10.1016/S0040-4020(01)88013-3

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 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 (CF₃Py-Nap-OH or CF₃Py-PyOH). Similarly, coupling of the 2-amino-5-CF₃-pyridyl) radical yields 3-heterobiaryl derivatives. Coupling of the malonate anion takes place with the aforementioned radicals.