Work

Photocatalytic delayed hydration by alkene-alkene coupling: Modular access to highly substituted γ- and δ-lactones

Year: 2025

Type: article

Abstract: γ- and δ-lactones are important core structures in a wide range of natural products and bioactive molecules. However, a gap remains for rapid access to γ- and δ-lactones from easily available and simple starting materials with tunability for substitution patterns. Here, a photocatalytic "streamlined sew" strategy of two alkenes with water for the synthesis of γ- and δ-lactones by a [1 + 2 + 2] or [1 + 2 + 3] cyclization has been developed. The reaction features the delayed hydration of alkenes by differentiating different alkyl radicals to undergo chemo- and regioselective alkene-alkene cross-coupling. Notably, styrenes, tetra-, tri-, and disubstituted aliphatic alkenes are tolerated in the reaction, allowing for rapid and modular assembly of γ- and δ-lactones from two alkenes in the presence of water.

Source: Science Advances

DOI: 10.1126/sciadv.aea1708

Authors: Yu-Feng Ren, Jin-Kui Chen, Xiao-Yi Chen, Hai-Wu Du, Qiong Yu, Wei Shu

Institutions: Southern University of Science and Technology, Sichuan University of Science and Engineering

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $4,500