Enhanced Decarboxylative Sulfonylation of Cinnamic Acids to (E)-Vinyl Sulfones via Manganese-doped Mesoporous Beta Zeolite Catalyst

Abstract

Vinyl sulfones are pivotal as chemical feedstocks and intermediates in pharmaceutical synthesis. However, current synthetic methods predominantly rely on homogeneous transition metal salt catalysts and costly organic ligands, significantly limiting their industrial feasibility. This study introduces an acidic heterogeneous Mn-Beta zeolite catalyst with a mesoporous structure, prepared via an in-situ doping method. The catalyst demonstrates remarkable efficiency in catalyzing the decarboxylative sulfonylation of cinnamic acid with sodium benzenesulfinate, achieving isolated yields of up to 86% for (E)-vinyl sulfones. Notably, the reaction exhibits a broad substrate scope and exceptional functional group tolerance. The coordination of Mn within the Mn-Beta framework plays a crucial role in reactant activation, and further in-situ XPS characterization confirms that Mn(II) species remain the key active sites throughout the catalytic transformation, ensuring consistent performance. The catalyst shows outstanding stability and can be reused multiple times without significant loss of activity. The findings presented herein offer valuable insights into the development of zeolite-based catalysts for the synthesis of vinyl sulfone compounds. It is expected that this work will inspire further advancements in the design and application of heterogeneous catalysts for sustainable and efficient chemical synthesis.

Keywords

Vinyl sulfone / Mn-Beta zeolite / Heterogeneous catalysis / Decarboxylative sulfonylation

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Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH