Copper-Catalyzed Cascade Phosphorodithiolation/Cyclization of β-Ketodinitriles: Organic Transformation of P4S10
Minjing Yuan , Longzhi Zhu , Weifeng Xu , Yilong Zeng , Guo-Liang Lu , Biquan Xiong , Renhua Qiu
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (17) : 2159 -2166.
Copper-Catalyzed Cascade Phosphorodithiolation/Cyclization of β-Ketodinitriles: Organic Transformation of P4S10
An innovative approach to synthesizing pyrrole-functionalized phosphorodithioates via a copper-catalyzed cascade phosphorodithiolation/cyclization of β-ketodinitriles is disclosed. This method employs tetraphosphorus decasulfide (P4S10) as a phosphorus source, activated by alcohols under mild conditions. A wide range of β-ketodinitriles and alcohols are well-tolerated, affording the desired products with good to excellent yields, underscoring broad functional group compatibility. Notably, this process eschews the need for noble metal catalysts, aligning with green chemistry principles by enabling a direct and sustainable transformation from inorganic to organic phosphorus. Furthermore, the synthesized pyrrole-functionalized phosphorodithioates demonstrate potent antibacterial properties against Staphylococcus aureus.
Tetraphosphorus decasulfide / Alcohols / Copper catalysis / Phosphorodithiolation / Multicomponent reactions / Cyclization
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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