Synthesis of β‐Phenylchalcogeno‐α,β‐unsaturated Ketones via Hydrochalcogenation of Acetylenes using Microwave and Solvent‐Free Conditions

Abstract

A simple, clean, and efficient solvent‐free protocol was developed for hydrochalcogenation of 3‐organyl‐3‐butyn‐2‐ones with phenylchalcogenolate (Se, Te, S) anions generated in situ from the respective diphenyl dichalcogenide using alumina‐supported sodium borohydride (Se, Te) or commercially available (S). This efficient and improved method is general and furnishes the (Z)‐β‐phenylchalcogeno‐α,β‐unsaturated ketones in good yield with higher selectivity compared with those that use organic solvent and an inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.

Keywords:

• Solvent‐free
• microwave
• chalcogen compounds

Acknowledgments

This project is funded by Fundação de Amparo à Pesquisa do RS (FAPERGS), Conselho Nacional de Desenvolvimento Cientifico e Tecnológico (CNPq), and a grant from the Chemical Research Applied to World Needs Future Actions Committee (ChemRAWN XIV) International Green Chemistry Grants Program.