I2-Photocatalyzed Cascade Reaction of 1-Isothiocyanatonaphthalenes with Amines to Give Naphtho[1,2- d ]thiazol-2-Amines

Abstract Visible light initiates an I2-photocatalyzed cascade reaction of 1-isothiocyanatonaphthalenes and amines using O2 as the oxidant to N-substituted naphtho[1,2-d]thiazol-2-amines in good to excellent yields. This methodology is operationally simple, exhibits excellent functional group tolerance, and proceeds efficiently on a gram scale. The mechanism involves oxidation of the anion of in situ-formed N-(naphthalen-1-yl)carbothioamide by 1O2 photosensitized by *I2 or single-electron transfer from the excited charge-transfer complex between I2 and N-(naphthalen-1-yl)carbothioamide to give a sulfur radical that adds to the naphthalene ring, followed by rearomatization to give the product.