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Pd-Catalyzed Decarbonylative <i>sp</i><sup>2</sup> C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds

Shan‐Shan Zhang, Mengjie Cen, Chenglong Li, Long Liu, Tianzeng Huang, Tieqiao Chen

2024Organic Letters12 citationsDOI

Abstract

The cyclic compounds have wide applications in the design and synthesis of drugs and materials; thus, their efficient construction attracts much attention from the synthetic community. In this letter, we report an efficient method for preparing cyclic compounds starting from the readily available carboxylic acids. This reaction takes place through intramolecular decarbonylative sp 2 C–H arylation, enabling efficient synthesis of a wide range of five- and six-membered cyclic compounds. Both carbo- and heterocycles can be produced under the reaction conditions. Moreover, this reaction features a wide substrate scope with high functional group tolerance. The scale-up experiments also show its practicality in organic synthesis. Those experimental results indicate that this reaction would find wide applications in the synthetic community.

Topics & Concepts

ChemistryCatalysisMedicinal chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions
Pd-Catalyzed Decarbonylative <i>sp</i><sup>2</sup> C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds | Litcius