Transition-metal catalyzed oxidative spirocyclization of N-aryl alkynamides with methylarenes under microwave irradiation

Abstract

A practical synthetic route to construct a variety of 3-benzyl spiro[4,5]trienones was developed via transition-metal Cu/Ag-catalyzed oxidative ipso-annulation of activated alkynes with unactivated toluenes using TBPB as an oxidant under microwave irradiation. This method allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling, ipso-carbocyclization and dearomatization. The advantages of this protocol are its operational simplicity and broad substrate scope, and the ability to afford the desired products in moderate to good yields.