Silver-catalyzed chemodivergent assembly of aminomethylated isochromenes and naphthols

Abstract

A silver-catalyzed chemodivergent cyclization of alkyne-tethered aldehydes with aminals to aminomethylated 1H-isochromenes and naphthols is described by tuning the reaction conditions. The reaction exhibits broad substrate generality and functional group compatibility. Mechanistic studies have disclosed that the aminomethylated naphthols are generated from the resulting N,O-aminal containing isochromenes via a silver-catalyzed unusual rearrangement process.