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Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO <sub>2</sub> as a CO Surrogate

Yanhui Guo, Wei Li, Huanfeng Jiang, Chaorong Qi

2024Asian Journal of Organic Chemistry11 citationsDOI

Abstract

Abstract Palladium‐catalyzed carbonylation of aryl sulfonium salts with CO 2 as a CO surrogate has been successfully developed via a one‐pot two‐step procedure. Thus, by merging thianthrenation and the carbonylation, site‐selective aromatic C−H carbonylation of a plethora of readily available arenes can be realized with CO 2 , providing access to a variety of structurally diverse and useful benzamides, esters and carboxylic acids. Simple operation, broad substrate scope, good functional group tolerance and mild reaction conditions are the attractive features of the method. Late‐stage functionalization of complex bioactive molecules as well as the precise synthesis of pharmaceuticals 1‐BCP and butoxycaine demonstrated the potential application of the established protocol.

Topics & Concepts

ChemistryCarbonylationArylPalladiumCatalysisSulfoniumOrganic chemistryCombinatorial chemistryCarbon monoxideAlkylSalt (chemistry)Carbon dioxide utilization in catalysisAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions
Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO <sub>2</sub> as a CO Surrogate | Litcius