Efficient Synthesis of β-Hydroxy Sulfides and β-Hydroxy Sulfoxides Catalyzed by Cu/MgO Under Solvent-Free Conditions

Abstract

Regio-, stereo-, and chemoselective ring opening of epoxides with thiols using Cu/MgO as a heterogeneous catalyst has efficiently been carried out to produce the corresponding β-hydroxy sulfides in excellent yields at room temperature under solvent-free conditions. The treatment of the epoxides with thiols and 50% aqueous H₂O₂ in the presence of the same catalyst at room temperature affords the β-hydroxy sulfoxides in excellent yields.

Keywords:

• Cu/MgO
• epoxide
• H₂O₂
• β-hydroxy sulfide
• β-hydroxy sulfoxide
• thiol

ACKNOWLEDGMENTS

The authors thank the Council of Scientific and Industrial Research and the University Grants Commission, New Delhi, for financial assistance.

Notes

^a The structures of the products were established from their spectral (¹H NMR and MS) data.

^b Yields reported in the parentheses are for other regioisomers.

^a The structures of the products were established from their spectral (¹H NMR and MS) data.

^b Diastereomeric (82:18) mixture determined by ¹H NMR analysis.

Part 170 in the series “Studies on Novel Synthetic Methodologies.”