Phosphinoferrocenyl-terminated amidoamines: Synthesis and catalytic utilization in palladium-mediated C–C bond forming reactions

✍ Scribed by Janett Kühnert; Martin Lamač; Jan Demel; Anja Nicolai; Heinrich Lang; Petr Štěpnička

• Book ID: 103834882
• Publisher: Elsevier Science
• Year: 2008
• Tongue: English
• Weight: 359 KB
• Volume: 285
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/j.molcata.2008.01.026

✦ Synopsis

1 -(Diphenylphosphino)-1-(N-butylcarbamoyl)ferrocene (P1) and the analogous higher amides P2-4 related to the first-generation PAMAM dendrimers bearing up to four 1 -(diphenylphosphino)ferrocen-1-yl terminal groups were synthesized by amidation of the respective (poly)amines with 1 -(diphenylphosphino)ferrocenecarboxylic acid (Hdpf). Testing of amides P1-4 as ligands for palladium-catalyzed Suzuki and Heck coupling reactions has shown that these amidophosphines preserve the activity of the single phosphinoferrocenyl unit, giving rise to active catalysts in both C-C forming reactions. Even for such relatively small systems, a positive influence of the dendritic assembly was notable as the compounds bearing a higher number of the phosphinoferrocenyl termini afforded faster reacting catalytic systems at the same palladium loading and P-to-Pd ratio.