Metal‐Free Reagent Dependent SS and CC Homocoupling of α‐Enolic Dithioesters at Room Temperature: Direct Access to Fully Substituted Symmetrical Thiophenes via Chemoselective Paal–Knorr Approach

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An unprecedented metal‐free oxidative homodimerization of α‐enolic dithioesters has been achieved for the first time at room temperature within 5–10 min. Molecular iodine promotes the SS coupling leading to S , S ′‐bis(dithioacetals), while N ‐chlorosuccinimide facilitates CC coupling to give α,α′‐bis(β‐oxo dithioesters) in good to excellent yields. Furthermore, the newly generated α,α′‐bis(β‐oxo dithioesters) have been directly employed in the synthesis of fully substituted thiophenes with a unique symmetrical substitution pattern in a one‐pot, two‐step reaction sequence. magnified image