Silver-Catalyzed Skeletal Editing of Benzothiazol-2(3H)-ones and 2-Halogen-Substituted Benzothiazoles as a Rapid Single-Step Approach to Benzo[1,2,3]thiadiazoles

A facile silver(I)-catalyzed reaction of benzothiazol-2(3H)-ones with NaNO2, or using AgNO2 directly, enables a single-step transformation to the corresponding benzo[1,2,3]thiadiazoles in moderate to excellent yields, with wide functional group compatibility. It can also be performed in a one-pot manner from readily available 2-halobenzothiazoles. This intriguing transformation involving an atom replacement in the S,N-heteroarene ring thus provides rapid access to isobenzothiadiazoles (while avoiding the usage of unstable precursors) and also expands the toolbox of modern skeletal editing reactions.