Application of Metal–Organic Frameworks in Multicomponent Reactions

Abstract

Metal-catalyzed multicomponent reactions are versatile synthetic protocols often used to prepare a range of different products. These reactions provide complete molecular diversity and high atom efficiency while saving energy. Recently, metal–organic frameworks have attracted attention as environmentally friendly catalytic systems as they possess an abundance of catalytic sites in ordered crystal skeletons. In this graphical review, we highlight the recent progress made utilizing metal–organic frameworks to facilitate multicomponent reactions.

Key words

metal–organic frameworks - multicomponent reactions - heterogeneous catalysis - transition-metal catalysts - organic linkers

Biosketches

Younes Latifi was born in Dezful, Iran, in 2001. He earned his Bachelor’s degree from Shahid Chamran University in Ahvaz, Iran. In 2023, he joined Prof. Teimouri’s research group and is currently a Master’s student in organic chemistry at Kharazmi University, Tehran, Iran. His research interests include multicomponent reactions and activities related to the field of green chemistry.

Mahdi Behraveshfar was born in Kermanshah, Iran, in 1999. He received his Bachelor’s degree in 2022 from Payame Noor University of Karaj, Iran. In 2023, he joined Prof. Teimouri’s research group and is currently a Master’s student in organic chemistry at Kharazmi University in Tehran. His research interests include the synthesis of drug compounds using multicomponent reaction methods and suitable catalysts, such as metal–organic frameworks (MOFs).

Mohammad Bagher Teimouri was born in 1975 and studied chemistry at Tabriz University, Iran. He subsequently completed his Ph.D. in 2004 with Prof. Ahmad Shaabani at Shahid Beheshti University. After being an assistant professor at the Iran Polymer and Petrochemical Institute, he moved to Kharazmi University as an associate professor, where he was promoted to full professor in 2022. His research focuses on the development of new multicomponent reactions (MCRs), especially on isocyanide-based and enaminone-based MCRs, MCRs in/on water, stereoselective transformations and the synthesis of novel functional dyes.

Multicomponent reactions (MCRs) are chemical processes where several reactants are combined in one vessel to create a final product that contains most of the atoms from the starting materials. Such processes involve a series of chemical transformations without changing the reaction environment between steps. The result is a diverse range of molecules created more efficiently than traditional step-by-step methods. Compared to multistep synthetic processes, one-pot reactions improve efficiency, reduce waste production, and enable the rapid construction of more complex molecules from simple, readily available starting materials. This efficiency is particularly appealing in the pharmaceutical industry, where quickly creating large libraries of potentially useful compounds is important. Multicomponent reactions have been established incorporating three, four, or more components, and numerous studies have been reported on the development of new MCRs.

MCRs align with the fundamental principles of green chemistry by producing complex final products in a single step through innovative synthetic approaches that are environmentally sustainable. Some notable advantages of utilizing MCRs include generating less waste, conserving resources, and reducing energy requirements. These advantages have captured the attention of researchers aiming to develop cutting-edge green chemistry processes.

In recent years, metal–organic frameworks (MOFs) have become important in chemical research due to their large surface areas, high porosities, low densities, ease of separation, high crystallinities, and abundant catalytic metal centers. These specific properties, combined with the low solubility of MOFs, allow for their wide application as heterogeneous catalysts, facilitating their recovery and reuse. Hence, they are considered to be green and recyclable catalysts. MOFs are made from metal ions or clusters linked by organic molecules and are used in various sustainable technologies. The solvothermal method is commonly used to produce MOFs because it allows precise control over their shape and size. Additionally, microwave-assisted synthesis speeds up the process, resulting in high yields and well-defined properties.

In addition, MOFs are micro/mesoporous crystalline solids. Their lattice is formed by connecting metallic nodes, comprising metal cations or clusters of a few metal ions, with rigid organic linkers possessing two or more coordination positions. The organic linkers are incredibly diverse, mostly based on carboxylates, N-donor groups, or even phosphonates, and have a variety of configurations. MOFs, due to their high abundance, low cost, non-toxicity, and environmentally friendly nature, have attracted significant attention compared to noble-metal-based materials.

The specific choice of metal ions and organic linkers significantly affects the properties and functionality of MOFs. Metal–organic frameworks exhibit diverse properties based on the types of ligands and surface functional groups they possess. The porosities of MOFs can be adjusted by altering the size of these components. MOFs can also be modified either before or after they are made. Despite their advantages, MOFs face challenges in practical applications, including high production costs, chemical stability issues, and recycling difficulties. However, they show promise as recyclable green catalysts in multicomponent reactions due to their abundant acidic sites. The properties of MOFs bestow them with significant potential for various applications, such as in drug delivery and heterogeneous catalysis, and as heavy metal absorbents, supercapacitors, and sensors. Research in this area is still developing, and this graphical review highlights recent progress in using MOFs to facilitate MCRs.

Figure 1 Zn-containing metal–organic frameworks (part 1)[1`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 2 Zn-containing metal–organic frameworks (part 2)[2`] [b] [c] [d] [e] [f] [g]

Figure 3 Zn-containing metal–organic frameworks (part 3)[3`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Figure 4 Zn-containing metal–organic frameworks (part 4)[4`] [b] [c] [d] [e] [f] [g]

Figure 5 Zn-containing metal–organic frameworks (part 5)[5`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k]

Figure 6 Zr-containing metal–organic frameworks (part 1)[6`] [b] [c] [d] [e] [f] [g]

Figure 7 Zr-containing metal–organic frameworks (part 2)[5f] ^, [7`] [b] [c] [d] [e] [f] [g] [h]

Figure 8 Zr-containing metal–organic frameworks (part 3)[8`] [b] [c] [d] [e] [f] [g]

Figure 9 Zr-containing metal–organic frameworks (part 4)[9`] [b] [c] [d] [e] [f] [g] [h]

Figure 10 Zr-containing metal–organic frameworks (part 5)[6a] [7g] ^, [10`] [b] [c]

Figure 11 Cr-containing metal–organic frameworks (part 1)[11`] [b] [c] [d] [e] [f] [g] [h]

Figure 12 Cr-containing metal–organic frameworks (part 2)[5f] ^, [12`] [b] [c] [d] [e] [f] [g]

Figure 13 Cr-containing metal–organic frameworks (part 3)[11h] [13Å] [b] [c] [d] [e] [f] [g]

Figure 14 Cu-containing metal–organic frameworks (part 1)[14`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Figure 15 Cu-containing metal–organic frameworks (part 2)[15`] [b] [c] [d] [e] [f] [g] [h]

Figure 16 Cu-containing metal–organic frameworks (part 3)[16`] [b] [c] [d] [e] [f]

Figure 17 Fe-containing metal–organic frameworks (part 1)[6g] ^, [17`] [b] [c] [d] [e]

Figure 18 Fe-containing metal–organic frameworks (part 2)[5f] [12g] ^, [18`] [b] [c] [d] [e]

Figure 19 Co-containing metal–organic frameworks[3g] [5f] ^, [19`] [b] [c] [d] [e] [f]

Figure 20 In-containing metal–organic frameworks[20`] [b] [c] [d] [e] [f] [g] [h]

Figure 21 Ni-containing metal–organic frameworks[5f] ^, [21`] [b] [c] [d] [e]

Figure 22 Ti-, Al-, Mn-, and Bi-containing metal–organic frameworks[5f] [6g] [12g] ^, [22`] [b] [c] [d] [e] [f]

Figure 23 Cd-, Ag-, Ir-, Er-, and Ta-containing metal–organic frameworks[4f] [5f] ^, [23`] [b] [c] [d] [e]

Figure 24 Bimetallic metal–organic frameworks[5f] ^, [24`] [b] [c] [d]

Conflict of Interest

The authors declare no conflict of interest.

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Publication History

Received: 09 September 2024

Accepted after revision: 07 October 2024

Article published online:
09 December 2024