An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates

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 effect...

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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
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Abstract 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.
AbstractList 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.
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. [reaction: see text]
Author Shultz, C. Scott
Cai, Chaoxian
Balsells, Jaume
Sidler, Rick R
Sun, Yongkui
Rivera, Nelo R
McWilliams, J. Christopher
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Snippet Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered...
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SubjectTerms Arylsulfonates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Esters
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
Palladium
Tosyl Compounds - chemistry
Title An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates
URI http://dx.doi.org/10.1021/ol062208g
https://www.ncbi.nlm.nih.gov/pubmed/17048868
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