Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
Haonan Xiang, Jie Liu, Jieping Wang, Lvqi Jiang, Wenbin Yi
Abstract
A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barrier in the first step of deoxygenation. The mild deoxygenation process enables the reduction of a wide range of functionalized sulfonyl chlorides as well as sulfonic anhydrides. The novel method represents an operationally simple protocol using readily available reagents and exhibits broad functional group tolerance.
Topics & Concepts
DeoxygenationChemistrySulfonylElectrophileSquaric acidNucleophileReagentCombinatorial chemistrySulfonic acidOrganic chemistryCatalysisAlkylSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods