Coupling of Fischer carbene complexes with o-alkynylbenzamides

The coupling of 2-alkynylbenzamide derivatives with carbene complexes has been examined for systems that contain remote alkene functionality tethered either to the starting carbene complex or to the nitrogen of the amide. In most cases the reaction proceeds via alkyne insertion, followed by isobenzofuran formation, followed by intramolecular Diels-Alder reaction, followed by dehydration to afford aminonaphthalene derivatives. In examples using carbene complex tethered alkenes, intramolecular cyclopropanation is a competing reaction process.