New Chemical Transformations Involving SO₂ F₂ -Mediated Alcohol Activation

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Fluorine Chemistry

Background:

• Sulfuryl fluoride is a large-scale industrial fumigant.
• It exhibits unique stability and reactivity as a sulfur-based reagent.
• It serves as a triflate surrogate in organic synthesis.

Purpose of the Study:

• To highlight sulfuryl fluoride-mediated transformations in organic synthesis.
• To showcase its applications in metal-catalyzed reactions and nucleophilic substitutions.
• To compare fluorosulfonates with triflates and halides.

Main Methods:

• Metal-catalyzed transformations of aryl fluorosulfonates.
• One-pot processes from phenol derivatives.
• Nucleophilic substitution reactions on polyfluoroalkyl alcohols.

Main Results:

• Demonstrated efficient activation of alcohols and phenols to form fluorosulfonates.
• Developed metal-catalyzed reactions using aryl fluorosulfonates.
• Showcased the utility of polyfluoroalkyl fluorosulfonates in nucleophilic substitutions.

Conclusions:

• Sulfuryl fluoride is a valuable reagent for diverse synthetic applications.
• Fluorosulfonates offer advantages over triflates and halides in certain reactions.
• Industrial collaboration has driven significant advancements in sulfuryl fluoride chemistry.