Work

Fluoride‐Coupled Electron Transfer and Hydrogen‐Atom‐Transfer‐Mediated Synthesis of Difluoromethylarenes

Year: 2025

Type: article

Abstract: The difluoromethyl group is a bioisostere of hydroxy and sulfanyl groups. The photocatalytic reduction of trifluoromethyl groups is one of the most important methods for the synthesis of difluoromethyl compounds. We have developed a photoinduced synthesis of difluoromethyl compounds using a combined method of fluoride‐coupled electron transfer and hydrogen atom transfer. Utilizing benzimidazoline derivatives as photoreductant and hydrogen atom donor, difluoromethylarenes were synthesized through the C–F bond reduction of trifluoromethylarenes. Mechanistic studies indicated that the photoreduction proceeded via an electron‐donor–acceptor complex between trifluoromethylarenes and benzimidazoline derivatives.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202501034

Authors: Tatsuhiro Uchikura, Kaho Ohashi, Fua Akutsu, Takahiko Akiyama

Institution: Gakushuin University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Japan Society for the Promotion of Science London, Japan Society for the Promotion of Science