Published January 1, 2025
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Synthesis of Dithioester Derivatives by Base-Mediated Fragmentation of 1,3-Dithiolanes
Creators
- 1. Istanbul Tech Univ, Sci Fac, Dept Chem, TR-34469 Istanbul, Turkiye
Description
Dithioesters are important agents for chain transfer in polymer chemistry and precursors in the synthesis of heterocycles. Straightforward approaches to their synthesis are therefore in demand. Outlined herein is a method to access such compounds in one-pot. 2-Aryl-1,3-dithiolanes undergo ring fragmentation with LiHMDS in CPME to generate aryl-dithiocarboxylates in 5 min at 100 degrees C. These anions are subsequently captured in the second step by addition of various alkyl halides and diaryliodonium salts to furnish a large library of dithioesters in good yields. The method can be also employed in a one-pot, one-step manner for alkyl bromides and allows the synthesis of dithioesters in gram scale.
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