An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates

• Published in: Organic letters Vol. 8; no. 22; pp. 5161 - 5164
• Main Authors: Cai, Chaoxian, Rivera, Nelo R, Balsells, Jaume, Sidler, Rick R, McWilliams, J. Christopher, Shultz, C. Scott, Sun, Yongkui
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 26-10-2006
• Subjects: Arylsulfonates - chemistry; Catalysis; Combinatorial Chemistry Techniques; Esters; Hydrocarbons, Fluorinated - chemistry; Molecular Structure; Palladium; Tosyl Compounds - chemistry
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol062208g

Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.