Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)₂-Mediated Oxidative C–C Bond Formation

Abstract

The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp2)–C(sp2) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.