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Copper(I)-Catalyzed Sandmeyer-Type S-Arylation of 1-Thiosugars with Aryldiazonium Salts under Mild Conditions
Rapelly Venkatesh1, Varsha Tiwari1, Jeyakumar Kandasamy1
1Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh 221005, India.
Abstract:
Preparation of S-aryl thioglycosides from 1-thiosugars via S-arylation was demonstrated under mild reaction conditions. A wide range of protected and unprotected 1-thiosugars derived from glucose, glucosamine, galactose, mannose, ribose, maltose, and lactose underwent cross-coupling reactions with functionalized aryldiazonium salts in the presence of copper(I) chloride and DBU. The desired products were obtained in 55-88% yields within 5 min. Various functional groups, including halogens, were tolerated under standard reaction conditions. Synthesis of the biologically relevant antidiabetic dapagliflozin S-analogue and arbutin S-analogues (tyrosinase inhibitors) was demonstrated.
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