Regio- and stereoselective co-iodination of olefins using NH₄I and Oxone

ABSTRACT

A simple, efficient, and environmentally benign protocol for the synthesis of vicinal iodohydrins and iodoesters from olefins using NH₄I and Oxone in CH₃CN/H₂O (1:1) and dimethylformamide (DMF) / dimethylacetamide (DMA), respectively, without employing a catalyst at room temperature is described. Regio- and stereoselective iodohydroxylation and iodoesterification of various olefins with anti fashion, following Markonikov’s rule, was achieved and the corresponding products were obtained in good to excellent yields. In addition, 1,2-disubstituted olefins afforded excellent diastereoselectivity.

GRAPHICAL ABSTRACT

KEYWORDS:

• Co-iodination
• diastereoselectivity
• NH₄I
• olefins
• Oxone