AI Article Synopsis
- Nickel- and palladium-catalyzed Fukuyama coupling reactions effectively produced multifunctional aryl ketones from a specific thioester and arylzinc reagents at room temperature.
- The study identified 1,2-bis(dicyclohexylphosphino)ethane (dCype) as an excellent ligand to enhance product yields in the nickel-catalyzed reactions.
- Additionally, Pd/C was found to be a convenient alternative for ligand-free reactions, successfully aiding in the production of important diabetic medications like canagliflozin and dapagliflozin.
Article Abstract
Nickel- and palladium-catalyzed Fukuyama coupling reactions of a d-gluconolactone-derived thioester with arylzinc reagents at ambient temperature provided the corresponding multifunctional aryl ketones in high yield. Ligand screening for the nickel-catalyzed Fukuyama coupling reactions indicated that 1,2-bis(dicyclohexylphosphino)ethane (dCype) served as a superior supporting ligand to improve the product yield. In addition, Pd/C was a practical alternative that enabled ligand-free Fukuyama coupling reactions and was efficiently applied to the key C-C bond-forming step to prepare canagliflozin and dapagliflozin, which are diabetic SGLT2 inhibitors of current interest.
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| http://dx.doi.org/10.1021/acs.joc.0c01635 | DOI Listing |
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