Electroreductive hydroxy fluorosulfonylation of alkenes.

Area of Science:

• Organic Chemistry
• Electrochemistry
• Green Chemistry

Background:

• Hydroxyl fluorosulfonylation is a crucial transformation for synthesizing organofluorine compounds.
• Developing mild and efficient methods for this process remains a significant challenge in synthetic chemistry.

Purpose of the Study:

• To establish a novel electroreductive strategy for the radical hydroxyl fluorosulfonylation of alkenes.
• To explore the use of readily available reagents like sulfuryl chlorofluoride and molecular oxygen.

Main Methods:

• Employing an electroreductive approach for the reaction.
• Utilizing sulfuryl chlorofluoride (SO2ClF) as the fluorine and sulfonyl source.
• Incorporating molecular oxygen (O2) from air as an oxidant.

Main Results:

• Successful synthesis of diverse β-hydroxy sulfonyl fluorides with broad functional group tolerance.
• Demonstrated scalability of the protocol.
• Conversion of products to valuable aliphatic sulfonyl fluorides, β-keto sulfonyl fluorides, and β-alkenyl sulfonyl fluorides.
• Identified potent inhibitory activity of some products against Botrytis cinerea and Bursaphelenchus xylophilus.

Conclusions:

• The developed electroreductive strategy offers a mild, efficient, and scalable route to β-hydroxy sulfonyl fluorides.
• The products exhibit potential for agrochemical applications, particularly as fungicides and nematicides.
• Mechanistic studies suggest a radical pathway involving O2 interception and peroxy radical reduction.