Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether

Abstract

An FeCl₃-catalyzed allenic Claisen rearrangement/regio- and chemoselective aerobic dehydrogenative cyclization domino reaction is developed, providing a wide range of 2-aryl/alkyl, 3-(substituted-vinyl)naphtho[2,1- b]furans in high yields at 95-130 °C in an atom- and step-economic fashion. Mechanistic studies suggest that the FeCl₃ catalyst is responsible for the high regio- and chemoselectivity in reaction. A blue-emitting product shows quantum yield of 0.95. The reaction proceeds readily on the gram scale, and synthetic applications of the products are also demonstrated.