Electrochemical synthesis of isobenzofuran-1-imines using oxidative halocyclization of o-alkynylbenzamides

Abstract

Electrochemical oxidative 5-exo-dig-oxo-halocyclization of o-alkynylbenzamides was achieved using readily available NaX (X = Cl, Br and I) salts under mild reaction conditions. The use of a cheap and highly stable sodium halide as a halide ion source is impressive for the synthesis of a variety of halogenated isobenzofuran-1-imines. This electrochemical protocol shows regioselectivity and excellent conversion to isobenzofuran-1-imines in good yields without the use of stoichiometric amounts of oxidants and transition metal catalysts.