Work

Construction of Spirocyclic Compounds via Electrochemical Intramolecular Dearomatization of Benzene Derivatives

Year: 2024

Type: article

Abstract: The spirocyclic framework is found in many natural products, some of which are biologically active. However, It remains a challenge to develop environmentally friendly and atom‐economic synthetic methods. Herein, we report an intramolecular dearomatization reaction of benzene derivatives enabled by electrochemistry‐mediated two successive single‐electron‐transfer (SET) processes, providing an alternative method for the rapid construction of spirocyclic skeletons without using sacrificial reagents. A series of cyclohexadiene products were obtained in 25–81% yields. Furthermore, a proposed mechanism involving a sequential electron transfer event was supported by cyclic voltammetry experiments. This strategy features transition‐metal‐free conditions and easy handling, which will greatly enhance its practical utility.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202400700

Authors: Wen‐Yun Zhang, Long‐Hao Zhu, Yuan‐Zheng Cheng, Shu‐Li You

Institutions: Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, State Key Laboratory of Organometallic Chemistry

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality

Awards: G2701622746, G360593297, G387334713, G935704513