Domino (2 + 3) Cycloaddition/Self-Oxidation Reaction of S(IV) Intermediates α-Keto Sulfines with Thioureas for Access to Bisthiazole-5-yl Disulfides

This paper presents a novel, environmentally friendly, and efficient method for the construction of new thiazole disulfide skeletons via a domino formal (2 + 3) cycloaddition/self-oxidation reaction. Compared to previously reported methods, this approach offers several advantages, including eco-friendly solvents, mild reaction conditions, and a wide range of applicable substrates. We successfully synthesized a variety of thiazole disulfides with promising potential applications including their use in the late-stage functionalization of pharmaceuticals and natural products. Additionally, a series of control experiments were conducted to provide a deeper understanding of the cyclization/self-oxidation mechanism.