C-H Coupling Reactions Directed by Sulfoxides: Teaching an Old Functional Group New Tricks

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Sulfoxides are established functional groups for directing stoichiometric metalation and C-H bond functionalization.
• Recent synthetic methodologies have revitalized interest in sulfoxide reactivity.

Purpose of the Study:

• To review the recent advancements in sulfoxide-directed C-H functionalization.
• To highlight the versatility of sulfoxides in modern synthetic chemistry.

Main Methods:

• Catalytic C-H activation via internal sulfoxide coordination to metals.
• C-H functionalization through external sulfoxide ligands.
• Nucleophile and electrophile capture by sulfoxides to form sulfonium salts.

Main Results:

• Sulfoxides facilitate catalytic C-H activation through coordination or ligand action.
• Formation of sulfonium salts enables C-C bond construction at the expense of C-H bonds.
• Demonstrated versatility of sulfoxides in directing C-H functionalization.

Conclusions:

• Sulfoxides are experiencing a renaissance in their application for C-H functionalization.
• Their unique reactivity and versatility make them valuable tools in synthetic organic chemistry.