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- A novel method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is presented, utilizing t-BuXPhos as the effective biaryl phosphine ligand and K(3)PO(4) in tert-amyl alcohol as the best base-solvent combination.
- The reaction is compatible with a wide range of functional groups, including cyano, nitro, and aldehyde, and successfully couples various substrates, including electron-rich nonaflates and electron-poor sulfonamides, yielding high product amounts.
- The main limitation identified is the poor reactivity of 2,6-disubstituted aryl nonaflates, while kinetic
Article Abstract
A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K(3)PO(4) in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.
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| http://dx.doi.org/10.1021/jo200443u | DOI Listing |
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