Reaction of 1'-(diphenylphosphino)ferrocenecarboxylic acid (Hdpf) with mesoporous molecular sieve MCM-41 gives immobilized carboxyphosphine (3), which was further reacted with [{Ru(η6-p-cymene)Cl(µ-Cl)}2] (1) to afford Ru-phosphine modified molecular sieve 4. Material 4 was tested as a catalyst in the reaction of propargyl alcohol with benzoic acid in toluene to 2-oxopropyl benzoate (7).
The rate of the reaction with immobilized catalyst is slower and gives a lower yield compared with the homogeneous precatalyst [Ru(η6-p-cymene)(Hdpf-kP)Cl2] (2) prepared from Hdpf and dimer 1. The main reaction also competes with another parallel, propargyl alcohol consuming process, which occurs also with MCM-41 itself in an absence of benzoic acid.