Atom- and step-economic 1,3-thiosulfonylation of activated allenes with thiosulfonates to access vinyl sulfones/sulfides.

A new type of organocatalyzed 1,3-thiosulfonylation has been developed to straightforwardly access highly functionalized vinyl sulfones, which features mild conditions, atom- and step-economy, practicability, conciseness, and environmental friendliness. Moreover, these valuable products can be transformed to vinyl sulfides via a base-promoted isomerization. The versatile route can efficiently and rapidly introduce SCD3 groups with excellent levels of deuterium content (>99% D) by utilizing our newly developed SCD3 reagents. Gram-scale operations and further transformations are smoothly carried out, providing promising applications for drug discovery.

Citation

Xiao Xiao, Hong-Yu Tian, Yin-Qiu Huang, Yin-Jie Lu, Jing-Jie Fang, Gao-Jie Zhou, Fen-Er Chen. Atom- and step-economic 1,3-thiosulfonylation of activated allenes with thiosulfonates to access vinyl sulfones/sulfides. Chemical communications (Cambridge, England). 2022 Jun 09;58(47):6765-6768

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PMID: 35612002

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