Tandem Rearrangement and Acyl Transfer of N -Naphthylhydroxyl-amines with Amides to Access ortho -Amidinated Naphthol Esters

Abstract A metal- and oxidant-free synthesis of ortho-amidinated naphthol esters from readily available N-naphthylhydroxylamines and amides has been developed using fluorosulfuryl imidazolium triflate under mild conditions. This transformation provides a broad range of products in good yields with excellent ortho selectivity and broad functional group tolerance. A scale-up experiment further demonstrates the practicality of the protocol. Notably, this tandem process enables concurrent C1 esterification and ortho amidination of the naphthalene framework, providing an efficient strategy for the difunctionalization of naphthalene derivatives. The densely functionalized products obtained through this method may serve as useful building blocks in medicinal chemistry and organic synthesis.