Metal-free iodination of arylaldehydes for total synthesis of aristogins A–F and hernandial

Abstract

Iodine is one of the most effective sources for iodination of aromatic compounds; however, its electrophilicity is insufficient for direct iodination. The selection of appropriate environmentally friendly and cost-effective oxidants in combination with iodine for the iodination of aromatic rings, along with its application in the synthesis of natural products, holds significant importance. A highly efficient method utilizing I(III) as the initiator has been successfully developed for monoiodination of arylaldehydes. The method demonstrates good compatibility with a wide range of (hetero)aromatic aldehydes, resulting in moderate to excellent yields, without the need for any toxic, volatile or explosive reagents. The synthesis of seven natural products, namely aristogins A–F and hernandial, was achieved through this iodination followed by Ullmann-type coupling.