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Selective Monoacylation of Ferrocene with Bulky Acylating Agents over Mesoporous Sieve AlKIT‐5
Author(s) -
Procházková Dana,
Bejblová Martina,
Vlk Josef,
Vinu Ajayan,
Štěpnička Petr,
Čejka Jiří
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000218
Subject(s) - ferrocene , catalysis , acylation , chemistry , mesoporous material , mesoporous silica , molecular sieve , magic angle spinning , organic chemistry , mcm 41 , nuclear magnetic resonance spectroscopy , electrode , electrochemistry
Abstract Ferrocene acylation with bulky acylating agents (1‐adamantoyl, benzoyl, 2‐chlorobenzoyl, and cinnamoyl chlorides; and benzoic anhydride) catalyzed by AlKIT‐5 mesoporous catalysts was investigated. AlKIT‐5 catalysts with varying ratios of Si/Al were synthesized using tetraethoxysilane and aluminum isopropoxide as the structural building blocks and Pluronic F127 as a template under acidic conditions and were characterized in detail by X‐ray powder diffraction, magic‐angle spinning (MAS) NMR spectroscopy, sorption of nitrogen, energy‐dispersive X‐ray spectroscopy (EDS), SEM, TEM, and FTIR with pyridine as a probe molecule. The catalytic activity of the prepared AlKIT‐5 catalysts in ferrocene acylation was shown to depend on the type of the acylating agent, thus likely reflecting the strength of interactions between the acyl source, the product, and the solid catalysts when the acylation reaction was carried out at 100 °C. In all reactions, the AlKIT‐5 catalysts afforded exclusively the monoacylated products (100 % selectivity) most likely due to deactivation of the second cyclopentadiene ring by attachment of the first acyl group, steric reasons, and some competitive interactions of the monoacylferrocenes with the catalysts. The prepared AlKIT‐5 catalysts could be regenerated without any significant loss of the ferrocene conversion.