Stereoselective thiosulfonylation of alkynes using sodium thiosulfate as a sulfur transfer agent to access
Shashikant Tiwari1, Nitin Kumar1, Diwan S Rawat1,2
1Department of Chemistry, University of Delhi, Delhi-110007, India. dsrawat@chemistry.du.ac.in.
Abstract:
Here, we describe a novel and untapped reactivity profile of sodium thiosulfate, where it acts as an odourless, inexpensive and green sulfur surrogate equivalent to hydrogen sulfide (H2S) for in situ-generated iodo vinyl sulphones under metal and acid-free conditions. However, in contrast to acetic anhydride and alkyl halides, the utilisation of Na2S2O3 as a sulfurating agent with vinyl halides is quite rare. This methodology opens an avenue for the direct thiosulfonylation of a wide range of terminal or internal alkynes to get numerous bis (Z)-vinyl sulphones decorated with vicinal thioethers under environmentally benign conditions.
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