Ketyl Radical Coupling Enabled by Polycyclic Aromatic Hydrocarbon Electrophotocatalysts

Area of Science:

• Organic Chemistry
• Photocatalysis
• Electrochemistry

Background:

• Ketyl radicals are crucial intermediates in organic synthesis.
• Generating ketyl radicals from unactivated carbonyl compounds is challenging.
• Existing methods using reductants like SmI2/HMPA have limitations.

Purpose of the Study:

• To introduce a new class of electrophotocatalysts for carbonyl reduction.
• To enable challenging intermolecular ketyl radical coupling reactions.
• To expand the scope of reactive radical intermediates accessible via electrophotocatalysis.

Main Methods:

• Utilizing polycyclic aromatic hydrocarbons as electrophotocatalysts.
• Electrophotocatalytic reduction of unactivated carbonyl compounds.
• Demonstrating intermolecular ketyl radical coupling reactions.

Main Results:

• Successfully generated versatile ketyl radical intermediates from unactivated carbonyl compounds.
• Achieved intermolecular ketyl radical coupling reactions previously unsuccessful with classic reductants.
• Established a method to generate reactive radical intermediates without rapid mesolytic cleavage.

Conclusions:

• Polycyclic aromatic hydrocarbons represent a novel class of electrophotocatalysts.
• This catalytic platform overcomes limitations of traditional reductants for ketyl radical chemistry.
• The study broadens the utility of electrophotocatalysis for generating diverse radical species.