Abstract
Functionalised metal-organic frameworks (MOFs) which contain amino groups on their secondary building units (SBUs) are basic catalysts in the Knoevenagel condensation. University of Michigan Crystalline Material-1-amine (UMCM-1-NH2), Isoreticular MOF-3 (IRMOF-3) and a 5 % IRMOF-3 mixed in Isoreticular MOF-1 (MIXMOF) were evaluated as solid basic catalysts and demonstrated to be more active than aniline, their homogenous anologue. UMCM-1-NH2’s performance was higher than that of the other MOFs studied. IRMOF-3 and MIXMOF proved to have equal catalytic ability. Their catalytic performance was monitored at various temperatures and in different solvents for the reaction between benzaldehyde and ethyl acetoacetate or ethyl cyanoacetate.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Derouane EG, Roberts SM (2007) Catalysts for fine chemical synthesis, microporous and mesoporous solid catalysts. Wiley, West Sussex
Ernst S, Hartmann M, Sauerbeck S, Bongers T (2000) Appl Catal A 200:117–123
Rao YVS, De Vos DE, Jacobs PA (1997) Angew Chem Int Ed 36:2661–2663
Solomons TWG, Fryhle C (2009) Organic chemistry, 10th edn. Wiley, New York
Gascon J, Aktay U, Hernandez-Alonso MD, van Klink GPM, Kapteijn F (2009) J Catal 261:75–87
Corma A, Fornes V, Martin-Aranda RM, Garcia H, Primo J (1990) J Appl Catal 59:237
Kleist W, Maciejewski M, Baiker A (2010) Thermochim Acta 499:71–78
Koh K, Wong-Foy AG, Matzger AJ (2008) Angew Chem Int Ed 47:677–680
Freeman F (1980) Chem Rev 80:329–350
Tietze LF (1996) Chem Rev 96:115–136
Macquarrie DJ, Jackson DB, Clark JH (2001) In: Sherrington DC, Kybett AP (eds) Supported catalysts and their application. RSC, Cambridge
Corma A, Iborra S, Rodriguez I, Sanchez F (2002) J Catal 211:208–215
Climent MJ, Corma A, Dominguez I, Iborra S, Sabater MJ, Sastre G (2007) J Catal 246:136–146
Nguyen LTL, Le KKA, Truong HX, Phan NTS (2012) Catal Sci Technol 2:521–528
Brown WH, Foote CS, Iverson BL, Anslyn EV, Novak BM (2011) Organic chemistry, 6th edn. Brooks/Cole, Belmont
Sheldon RA, van Bekkum H (2008) Fine chemicals through heterogenous catalysis. Wiley, Weinheim
Hwang YK, Hong DY, Chang JS, Jhung SH, Seo YK, Kim J, Vimont A, Daturi M, Serre C, Ferey G (2008) Angew Chem Int Ed 47:4144–4148
Opanasenko M, Dhakshinamoorthy A, Shamzhy M, Nachtigall P, Horáček M, Garcia H, Čejka J (2013) Catal Sci Technol 3:500–507
Martín-Aranda RM, Čejka J (2010) Top Catal 53:141–153
Acknowledgments
Funding from the South African NRF, Sasol R&D and the research fund from the University of Johannesburg are gratefully acknowledged. ARB is grateful to the NRF-DAAD for a scholarship. Mr. D. Harris and Dr. R. Meyer (Shimadzu South Africa) are acknowledged for use of their equipment.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Burgoyne, A.R., Meijboom, R. Knoevenagel Condensation Reactions Catalysed by Metal-Organic Frameworks. Catal Lett 143, 563–571 (2013). https://doi.org/10.1007/s10562-013-0995-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-013-0995-5