Water-promoted C-S bond formation reactions

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Allylic sulfones are prevalent in biologically active molecules, driving demand for efficient synthetic methods.
• Current synthetic routes often require harsh conditions, posing challenges for mild and sustainable synthesis.

Purpose of the Study:

• To develop a mild, metal-free synthetic strategy for allylic sulfones.
• To explore the ligation of sulfinic acids with allylic alcohols via dehydrative cross-coupling.

Main Methods:

• Metal-free dehydrative cross-coupling of sulfinic acids with allylic alcohols.
• Utilized neutral, aqueous media at room temperature.
• Employed Density Functional Theory (DFT) calculations to elucidate the reaction mechanism.

Main Results:

• Achieved high yields and excellent selectivity for various aliphatic and aromatic sulfinic acids with allylic alcohols.
• Demonstrated a practical, metal-free, and environmentally benign synthetic route.
• Confirmed the essential role of water as a promoter in the transformation.

Conclusions:

• The developed method provides an efficient and practical pathway for synthesizing allylic sulfones under mild, aqueous conditions.
• The reaction's simplicity, avoiding organic extraction and chromatography, highlights its utility.
• Water's catalytic role, facilitated by hydrogen bonding, is crucial for this C-S bond formation.