Selective monoacylation of ferrocene with bulky acylating agents over mesoporous sieve AlKIT-5

Prochazkova, Dana, Bejblova, Martina, Vlk, Josef, Vinu, Ajayan, Stepnicka, Petr and Cejka, Jiri (2010) Selective monoacylation of ferrocene with bulky acylating agents over mesoporous sieve AlKIT-5. Chemistry: A European Journal, 16 26: 7773-7780. doi:10.1002/chem.201000218


Author Prochazkova, Dana
Bejblova, Martina
Vlk, Josef
Vinu, Ajayan
Stepnicka, Petr
Cejka, Jiri
Title Selective monoacylation of ferrocene with bulky acylating agents over mesoporous sieve AlKIT-5
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 0947-6539
1521-3765
Publication date 2010-01
Sub-type Article (original research)
DOI 10.1002/chem.201000218
Volume 16
Issue 26
Start page 7773
End page 7780
Total pages 8
Place of publication Weinheim, Germany
Publisher Wiley
Language eng
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.
Keyword Acylation
Aluminum
Ferrocene
Mesoporous materials
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Australian Institute for Bioengineering and Nanotechnology Publications
 
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