Litcius/Paper detail

Dearomatization of (Hetero)arenes through Photodriven Interplay between Polysulfide Anions and Formate**

Eugene Yew Kun Tan, Amirah S. Mat Lani, Wayne Sow, Yuliang Liu, Haoyu Li, Shunsuke Chiba

2023Angewandte Chemie International Edition27 citationsDOIOpen Access PDF

Abstract

)-rich carbo- and heterocyclic compounds is a pivotal synthetic strategy to foster contemporary drug discovery programs. The downstream dearomatization of readily accessible two-dimensional (2D) planar arenes represents a direct pathway towards accessing three-dimensional (3D) aliphatic scaffolds. Here, we demonstrate that polysulfide anions are capable of catalyzing a dearomatization process of substituted naphthalenes, indoles, and other related heteroaromatic compounds in the presence of potassium formate and methanol under visible light irradiation. The developed protocol exhibits broad functional group tolerance, operational simplicity, scalability, and cost-effectiveness, representing a practical and sustainable synthetic tool for the arene dearomatization.

Topics & Concepts

PolysulfideChemistryFormateCombinatorial chemistryMethanolOrganic chemistryCatalysisElectrodePhysical chemistryElectrolyteSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCovalent Organic Framework Applications