TBA−Br and Selectfluor Mediated Bromination of Glycals and Heterocyclic Compounds: Substrate Scope and Synthetic Utility

Abstract

AbstractHerein, we have devised a metal‐free stereoselective protocol mediated by selectfluor for the dibromination of sugar enol‐ethers and monobromination of heterocyclic compounds. The dibromination of glycals was achieved within 5 minutes at room temperature with excellent yields. The tolerance of various protecting groups such as acetyl, benzyl, and silyl in sugars was checked. When the same reagent system was applied to substituted indoles and chromones 3‐brominated products were obtained but at elevated temperatures. The synthetic utility of the methodology was demonstrated by using the brominated indoles and chromones to synthesize the 3‐aryl indoles and isoflavones respectively via Suzuki‐Miyura cross‐coupling reactions.