A General Approach to Site-Specific, Intramolecular C-H Functionalization Using Dithiocarbamates

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Intramolecular hydrogen atom transfer enables site-specific functionalization of C-H bonds.
• Existing methods often rely on unstable intermediates and strong oxidants, limiting scope to halogenations or aminations.

Purpose of the Study:

• To develop a novel, versatile C-H functionalization strategy.
• To expand the synthetic scope and convergency of reactions involving intramolecular hydrogen atom transfer.

Main Methods:

• Utilized stable, isolable N-dithiocarbamates as precursors.
• Generated amidyl radicals via light or radical initiation.
• Applied the method to a diverse range of complex structures.

Main Results:

• Achieved efficient delivery of versatile alkyl dithiocarbamates.
• Demonstrated site-specific C-H functionalization with increased synthetic scope.
• Successfully functionalized unactivated, aliphatic C-H bonds.

Conclusions:

• The developed method offers a robust and versatile approach for C-H functionalization.
• Stable precursors and radical initiation provide a safer and broader alternative to traditional methods.