Mechanochemical Synthesis of β-Sulfenylated Ketones and Esters

ChemSusChem. 2024 Oct 8:e202401591. doi: 10.1002/cssc.202401591. Online ahead of print.

Abstract

For the first time, ball milling has been employed in the solvent-free synthesis of sulfur-functionalized materials from thiols and α,β-unsaturated ketones and esters, using potassium carbonate as a transition metal-free catalyst. This environmentally friendly protocol makes use of easily accessible reagents to prepare thirty β-sulfenylated carbonyl compounds with yields exceeding 91 % under ambient air and solvent-free conditions. Additionally, this innovative synthetic strategy enables the modification of chalcones, compounds with significant medicinal and synthetic potential. The reactions are efficient and easily scalable to gram quantities, offering substantial benefits for practical applications.

Keywords: Esters; Hydrothiolation; Ketones; Mechanochemistry; Solid-state synthesis.