Journal
ORGANOMETALLICS
Volume 40, Issue 8, Pages 1129-1147Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.1c00091
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Funding
- Agence Nationale de la Recherche (Ferrodance project)
- Universite de Rennes 1
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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.
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.
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