One-Pot Protocol for Synthesis of α-Organosulfonyloxy Ketones from Secondary Alcohols Using Hypervalent Iodine(V)–Mediated Oxidations

Abstract

α-Tosyloxy ketones and α-mesyloxy ketones were directly prepared from alcohols in one pot by treatment with hypervalent iodine(V) reagents in combination with p-toluenesulfonic acid and methanesulfonic acid, respectively, in moderate to good yields. Reactions were also feasible under solvent-free conditions.

Keywords:

• Alcohols
• Dess–Martin periodinane
• hypervalent iodine(V) reagents
• organosulfonic acids
• α-organosulfonyloxy ketones
• solvent-free reaction condition

ACKNOWLEDGMENTS

For financial assistance, S. S. D. thanks the World Bank for support under the Technical Education Quality Improvement Program (TEQIP), and S. N. H. thanks the Narotam Sekhsaria Foundation, Mumbai. We are also thankful to M/S Omkar Chemicals in Badlapur, Thane, India, for their generous gift of DMP.

Notes

^a Reactions were carried on a 5-mmol scale and with 3 equiv of reagents.

^b Isolated yields using column chromatography.

^a Reactions were carried out on a 5-mmol scale in CH₃CN at reflux temperature with DMP (3 equiv) and organosulfonic acid (3 equiv).

^b Products were characterized by ¹H NMR, IR, and physical constants.

^c Isolated yields were determined using column chromatography.

^a Reactions were carried out under solvent-free conditions on a 5-mmol scale with DMP (3 equiv) and organosulfonic acid (3 equiv) at rt.

^b Corresponding ketones were recovered in the range of 20–40%.