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Ni-Catalyzed Hydrosulfonylation of Alkenes with Aromatic Iodides and K<sub>2</sub>S<sub>2</sub>O<sub>5</sub>

Jun Zhang, Hui-Ling Ma, Chenxi Yang, Jie Dang, Jiemin Xia, Jie Wu

2023Organic Letters18 citationsDOI

Abstract

Hydrosulfonylation of alkenes with readily available aromatic iodides via a SO 2 -insetion strategy is presented. The combination of non-noble Ni catalysis with ( i Pr) 3 SiH as the final reductant enables the efficient formation of aryl and heteroaryl sulfinate intermediates, which undergo Michael-type additions to electron-deficient alkenes for initiating the hydrosulfonylation process. Moreover, the superiority of this protocol is demonstrated by broad substrate scope and good functional group compatibility.

Topics & Concepts

ChemistryCatalysisArylCombinatorial chemistryCompatibility (geochemistry)Medicinal chemistryOrganic chemistryChemical engineeringAlkylEngineeringSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCyberloafing and Workplace Behavior
Ni-Catalyzed Hydrosulfonylation of Alkenes with Aromatic Iodides and K<sub>2</sub>S<sub>2</sub>O<sub>5</sub> | Litcius