Cu-doped zeolitic imidazolate framework catalysed highly selective conversion of alkynes to $$\upbeta $$ β -keto and vinyl sulfones using sodium sulfinates

Abstract

Cu 2+ -doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β-keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions has been described. The advantages of this protocol included broad substrate scope and excellent β-keto and E-stereoselectivity. The Cu/ZIF-8 catalyst not only exhibited excellent performance but also had a great stability in the reaction, successfully allowing its reuse up to five cycles. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time to generate β-keto and vinyl sulfones.

Advances in Vinyl Sulfone Catalyzed Synthesis: Methods, Mechanisms and Perspectives

“…The breakthrough achieved the formation of gold-catalyzed intermolecular CÀ S bonds. Therefore, in addition to palladium and copper, which are the two favored metal catalysts, the synthesis scheme of vinyl sulfones also proposes the use of other metal catalysts, such as Ag, Mn, Co, Au, etc., [49][50][51] which enriches the synthetic route as well as the variety of synthetic vinyl sulfones.…”

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…The Ponnapalli group demonstrated the Cu 2+ -doped zeolitic imidazolate framework-8 (Cu 25% /ZIF-8)-catalyzed oxysulfonylation and hydrosulfonylation of terminal alkynes with sulfinate salts in MeOH and MeCN, respectively ( Scheme 133 ). 199 A range of substituted arylalkynes reacted with sodium benzenesulfinate and sodium p -toluenesulfinate to furnish β-keto sulfones in moderate to good yields. In contrast, the reaction performed in MeCN led to the formation of the corresponding vinyl sulfones with excellent E -selectivity in good to high yields.…”

Superoxide Dismutase‐like Activity of Zeolitic Imidazolate Framework Nanoparticles Comprising Biomimetic Imidazolato‐bridged CuZn Units

“…Schneider and colleagues first synthesized CuZn‐ZIF‐8 (also known as Cu‐doped ZIF‐8) and demonstrated its efficacy and reusability as a catalyst for [3+2] azide–alkyne cycloaddition [33] . Since then, CuZn‐ZIF‐8 has been utilized as catalysts for a wide range of reactions with redox‐active metal centers, including aerobic alkane oxidation [34] and alcohol, [35] β ‐ketosulfone synthesis from alkynes, [36] dehydrogenative coupling of silanes with alcohols, [37] and hydrogenation of alkenes, [38] and CO 2 reduction [39] …”