Copper‐Iodide‐ and Diorganyl‐Diselenide‐Promoted Cyclization of 2‐Alkynylphenols: Alternative Approach to 3‐Organoselanylbenzo[b]furans

Abstract

This paper describes an alternative method for the synthesis of 3‐organoselanylbenzo[b]furans through the intramolecular cyclization of 2‐alkynylphenols promoted by copper iodide and diorganyl diselenides. The cyclization reactions were carried out at room temperature in the absence of base and under air (open flask). This synthetic approach proved to be efficient with both diorganyl diselenides and 2‐alkynylphenols bearing electron‐neutral, electron‐donating, and electron‐withdrawing substituents. 2‐Phenyl‐3‐phenylselanylbenzo[b]furan was used as a synthetic precursor in organochalcogen–lithium exchange and bromination reactions, allowing the synthesis of functionalized benzo[b]furans in good yields.