Functionalization of N,N-Dialkylferrocenesulfonamides toward Substituted Derivatives

Despite the well-established pharmacological properties of aromatic sulfonamides and the interest of introducing ferrocene into drugs, ferrocene sulfonamides have scarcely been studied. General synthetic methods using lithium bases to perform sulfonamide-directed deprotolithiation or the halogen dance reaction are here reported for the functionalization of N,N-dialkylferrocenesulfonamides toward various polysubstituted derivatives. Postfunctionalization of the ferrocenyl iodides by cross-coupling and lithium/iodine exchange reactions were also considered. Finally, the ligand behavior of new ferrocene phosphines in palladium-catalyzed coupling reactions was studied, and the reaction outcomes are viewed in light of DFT calculations.

Automated summary

This study reported a general synthetic method for the functionalization of N,N-dialkylferrocenyl sulfonamides. Additionally, the ligand behavior of new ferrocene phosphines in palladium-catalyzed coupling reactions was investigated.