Yaoluo Hu, Ya Hong, Yuting Zheng, Yi Huang, Jixiang Chen, Xingxing Wu
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引用次数: 0
Abstract
Phenanthrenequinones (PQs) are extensively studied in synthetic chemistry and materials science, exhibiting noteworthy biological activities essential for drug discovery. The development of efficient synthetic methods for PQ preparation has thus garnered significant attention, particularly through metal-catalyzed transformations. In this study, we present an N-heterocyclic carbene organocatalytic approach that enables the rapid construction of a diverse range of PQs and their derivatives without the need for stoichiometric oxidants or metal mediators. Mechanistically, the initial carbene-catalyzed formation of a benzoin adduct between the aldehyde and ester is critical in initiating a subsequent annulation reaction involving an aryl radical species. Our method represents the first example on the direct construction of PQ frameworks from simple starting materials by means of small-molecule catalysts. Furthermore, the catalytically obtained PQ products exhibit notable antimicrobial activity against common plant pathogens, offering promising potential for agrochemical development.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.