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Recent advances in amine catalyzed aldol condensations

Bert Biesemans, Jeriffa De Clercq (UGent) , Christian Stevens (UGent) , Joris Thybaut (UGent) and Jeroen Lauwaert (UGent)
(2024) CATALYSIS REVIEWS-SCIENCE AND ENGINEERING. 66(2). p.401-483
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Abstract
During the past two decades, new insights have driven the development and optimization of aminated materials as aldol condensation catalysts. Amines, either primary or secondary, facilitate the reaction via an enamine mechanism. If the spatial placement with respect to the amine allows it, weak acid sites such as silanols or hydroxyls, can cooperate as hydrogen bond donors and aid in proton transfer steps. Furthermore, the reaction environment, i.e., support and solvent and their mutual interactions, is also a key determining factor. In particular, co-feeding small amounts of water suppresses the formation of inhibiting and site-blocking species. However, silica-based materials are susceptible to hydrolysis. This led to the development of water tolerant (bio)polymer supported amine catalysts which also exhibit selective component enrichment properties, opening up opportunities for further catalyst development.
Keywords
Process Chemistry and Technology, General Chemistry, Catalysis, Aldol condensation, heterogeneous catalysis, amine catalysis, cooperativity, stability, DIRECT ASYMMETRIC ALDOL, LAYERED DOUBLE HYDROXIDES, SOLID BASE CATALYST, POLYSTYRENE-SUPPORTED PROLINE, SELECTIVE SELF-CONDENSATION, MESOPOROUS SILICA, HETEROGENEOUS CATALYSTS, LIGNOCELLULOSIC BIOMASS, ENANTIOSELECTIVE ALDOL, COOPERATIVE CATALYSIS

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Citation

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MLA
Biesemans, Bert, et al. “Recent Advances in Amine Catalyzed Aldol Condensations.” CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, vol. 66, no. 2, 2024, pp. 401–83, doi:10.1080/01614940.2022.2048570.
APA
Biesemans, B., De Clercq, J., Stevens, C., Thybaut, J., & Lauwaert, J. (2024). Recent advances in amine catalyzed aldol condensations. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 66(2), 401–483. https://doi.org/10.1080/01614940.2022.2048570
Chicago author-date
Biesemans, Bert, Jeriffa De Clercq, Christian Stevens, Joris Thybaut, and Jeroen Lauwaert. 2024. “Recent Advances in Amine Catalyzed Aldol Condensations.” CATALYSIS REVIEWS-SCIENCE AND ENGINEERING 66 (2): 401–83. https://doi.org/10.1080/01614940.2022.2048570.
Chicago author-date (all authors)
Biesemans, Bert, Jeriffa De Clercq, Christian Stevens, Joris Thybaut, and Jeroen Lauwaert. 2024. “Recent Advances in Amine Catalyzed Aldol Condensations.” CATALYSIS REVIEWS-SCIENCE AND ENGINEERING 66 (2): 401–483. doi:10.1080/01614940.2022.2048570.
Vancouver
1.
Biesemans B, De Clercq J, Stevens C, Thybaut J, Lauwaert J. Recent advances in amine catalyzed aldol condensations. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING. 2024;66(2):401–83.
IEEE
[1]
B. Biesemans, J. De Clercq, C. Stevens, J. Thybaut, and J. Lauwaert, “Recent advances in amine catalyzed aldol condensations,” CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, vol. 66, no. 2, pp. 401–483, 2024.
@article{8748646,
  abstract     = {{During the past two decades, new insights have driven the development and optimization of aminated materials as aldol condensation catalysts. Amines, either primary or secondary, facilitate the reaction via an enamine mechanism. If the spatial placement with respect to the amine allows it, weak acid sites such as silanols or hydroxyls, can cooperate as hydrogen bond donors and aid in proton transfer steps. Furthermore, the reaction environment, i.e., support and solvent and their mutual interactions, is also a key determining factor. In particular, co-feeding small amounts of water suppresses the formation of inhibiting and site-blocking species. However, silica-based materials are susceptible to hydrolysis. This led to the development of water tolerant (bio)polymer supported amine catalysts which also exhibit 
selective component enrichment properties, opening up opportunities for further catalyst development.}},
  author       = {{Biesemans, Bert and De Clercq, Jeriffa and Stevens, Christian and Thybaut, Joris and Lauwaert, Jeroen}},
  issn         = {{0161-4940}},
  journal      = {{CATALYSIS REVIEWS-SCIENCE AND ENGINEERING}},
  keywords     = {{Process Chemistry and Technology,General Chemistry,Catalysis,Aldol condensation,heterogeneous catalysis,amine catalysis,cooperativity,stability,DIRECT ASYMMETRIC ALDOL,LAYERED DOUBLE HYDROXIDES,SOLID BASE CATALYST,POLYSTYRENE-SUPPORTED PROLINE,SELECTIVE SELF-CONDENSATION,MESOPOROUS SILICA,HETEROGENEOUS CATALYSTS,LIGNOCELLULOSIC BIOMASS,ENANTIOSELECTIVE ALDOL,COOPERATIVE CATALYSIS}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{401--483}},
  title        = {{Recent advances in amine catalyzed aldol condensations}},
  url          = {{http://doi.org/10.1080/01614940.2022.2048570}},
  volume       = {{66}},
  year         = {{2024}},
}
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