Visible Light-Promoted Aliphatic C-H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent

Area of Science:

• Organic Chemistry
• Photochemistry
• Synthetic Methodology

Background:

• Direct functionalization of C(sp3)-H bonds remains a significant challenge in organic synthesis.
• Developing mild and practical methods for C-H activation is crucial for efficient molecule construction.

Purpose of the Study:

• To establish a novel, mild, and practical photochemical method for the direct arylation of unactivated C(sp3)-H bonds.
• To enable the formation of C(sp3)-C(sp2) bonds using readily available starting materials and visible light.

Main Methods:

• Utilizing photochemistry with visible light irradiation.
• Employing Selectfluor as a hydrogen atom transfer reagent.
• Investigating the intermolecular arylation of diverse C(sp3)-H feedstocks with heteroarenes.

Main Results:

• Achieved direct arylation of unactivated C(sp3)-H bonds in alkanes, ketones, esters, and ethers.
• Demonstrated successful intermolecular C(sp3)-C(sp2) bond formation with a wide range of heteroarenes.
• Showcased the method's applicability to complex molecules and pharmaceutically relevant scaffolds.

Conclusions:

• The developed photochemical protocol offers a mild and practical route for C(sp3)-H arylation.
• This method provides a versatile strategy for synthesizing complex organic molecules and functionalizing heteroarenes.
• The use of visible light and Selectfluor presents an efficient approach to C-H functionalization.