Effective α-Tosyloxylation of Ketones Using 1,1,1-Trifluoro-2-iodoethane as Catalyst

Abstract

With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of α-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervalent iodine intermediate. The in situ–generated active iodine species then reacts with ketones to afford the corresponding α-tosyloxyketones in good yields.

GRAPHICAL ABSTRACT

Keywords:

• Catalysis
• hypervalent iodine intermediate
• α-tosyloxylation
• 1,1,1-trifluoro-2-iodoethane

Notes

^a Isolated yields.

^a Isolated yield.