Work

Photoexcited Cyanohydrin Anions Enable Redox-Neutral Acylarylation of Olefins

Year: 2025

Type: article

Abstract: The direct photoexcitation of anions generated by deprotonation of C-H bonds under visible light has been less explored. Herein, we report that cyanohydrins can be photoexcited by visible light irradiation upon deprotonation. The photoexcited cyanohydrin anions demonstrate exceptional reducing capabilities, facilitating the single-electron transfer to aryl halides under mild conditions. The generated persistent cyanohydrin radicals serve as versatile acyl radical precursors for redox-neutral three-component acylarylation of olefins with a broad substrate scope. This study establishes cyanohydrin anions as a new class of photoactive species, offering a sustainable strategy for C-C bond formation without external oxidants or transition metals.

Source: JACS Au

DOI: 10.1021/jacsau.5c00470

Authors: Lei Shen, Xiaotong Zhang, Shiyu Chen, Ling Yue, Kangjiang Liang, Chengfeng Xia

Institution: Yunnan University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: National Natural Science Foundation of China, Natural Science Foundation of Yunnan Province