Photocatalytic C-F alkylation; facile access to multifluorinated arenes

Area of Science:

• Organic Chemistry
• Photocatalysis
• Fluorine Chemistry

Background:

• Carbon-fluorine (C-F) bond functionalization is synthetically challenging due to C-F bond strength and regioselectivity issues.
• Highly fluorinated arenes offer pre-installed C-F bonds, but selective functionalization methods are needed to unlock their synthetic potential.

Purpose of the Study:

• To develop a selective C-F functionalization strategy for highly fluorinated arenes.
• To enable the formation of new carbon-carbon bonds using readily available alkenes.
• To showcase the utility of the developed method in synthesizing complex fluorinated molecules.

Main Methods:

• Photocatalytic reductive alkylation of highly fluorinated arenes with unactivated alkenes.
• Utilized mild reaction conditions with low catalyst loading (0.25 mol%).
• Synergistic application of photocatalysis and nucleophilic aromatic substitution (S_NAr) chemistry.

Main Results:

• Achieved efficient C-F functionalization, forming C-C bonds under mild conditions.
• Demonstrated broad functional group tolerance.
• Successfully synthesized elaborate (hetero)arenes containing 2-5 aryl-fluorine bonds.

Conclusions:

• Developed a novel and efficient photocatalytic method for selective C-F bond alkylation.
• The strategy effectively utilizes the synthetic potential of highly fluorinated arenes.
• The combined approach of photocatalysis and S_NAr chemistry provides access to complex fluorinated compounds.