Halogen-Bonding-Promoted Photoinduced C-X Borylation of Aryl Halide Using Phenol Derivatives

Area of Science:

• Organic Chemistry
• Photochemistry
• Catalysis

Background:

• Aryl halides are important synthetic intermediates.
• Developing efficient methods for C-X bond functionalization is crucial.
• Boronate esters are versatile building blocks in organic synthesis.

Purpose of the Study:

• To develop a novel photoinduced C-X borylation reaction of aryl halides.
• To utilize halogen-bonding (XB) complexes for this transformation.
• To provide concise access to boronate esters with broad functional group tolerance.

Main Methods:

• Formation of a halogen-bonding (XB) complex between aryl halide and 2-naphthol.
• Photoirradiation to induce electron transfer and C-X bond cleavage.
• Chemoselective borylation reaction.

Main Results:

• The study successfully achieved photoinduced C-X borylation of aryl halides.
• The method demonstrated high chemoselectivity and functional group tolerance.
• Mechanistic studies confirmed the formation of an electron donor-acceptor complex facilitating aryl radical generation via photoinduced electron transfer.

Conclusions:

• The developed method offers a novel and efficient route to synthesize boronate esters from aryl halides.
• The use of XB complexes provides a unique strategy for photoinduced C-X activation.
• This approach broadens the synthetic utility of aryl halides in organic chemistry.