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 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]
Cai
Chaoxian
C
Process Research, Merck Research Laboratories, Merck & Company, Inc., P. O. Box 2000, Rahway, NJ 07065, USA. chaoxian_cai@merck.com
Rivera
Nelo R
NR
Balsells
Jaume
J
Sidler
Rick R
RR
McWilliams
J Christopher
JC
Shultz
C Scott
CS
Sun
Yongkui
Y
D001190:Arylsulfonates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium; D014105:Tosyl Compounds / Q000737:chemistry*
D001190:Arylsulfonates; D004952:Esters; D006845:Hydrocarbons, Fluorinated; D014105:Tosyl Compounds; D010165:Palladium