Metal-Free Reagent Dependent SS and CC Homocoupling of α-Enolic Dithioesters at Room Temperature: Direct Access to Fully Substituted Symmetrical Thiophenes via Chemoselective Paal-Knorr Approach

Ramulu, B. Janaki ; Nagaraju, Anugula ; Chowdhury, Sushobhan ; Koley, Suvajit ; Singh, Maya Shankar (2015) Metal-Free Reagent Dependent SS and CC Homocoupling of α-Enolic Dithioesters at Room Temperature: Direct Access to Fully Substituted Symmetrical Thiophenes via Chemoselective Paal-Knorr Approach Advanced Synthesis & Catalysis, 357 (2-3). pp. 530-538. ISSN 1615-4150

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Official URL: http://doi.org/10.1002/adsc.201400828

Related URL: http://dx.doi.org/10.1002/adsc.201400828

Abstract

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.

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Deposited On:15 Jun 2021 07:07
Last Modified:15 Jun 2021 07:07

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