Recent Advances in Heterogeneous Porous Metal-Organic Framework Catalysis for Suzuki-Miyaura Cross-couplings

Overview

Journal Heliyon

Specialty Social Sciences

Date 2024 Dec 17

PMID 39687170

Authors

Ravulakollu Srinivasa Rao

Mahira Bashri

Mohamed Infas Haja Mohideen

Ibrahim Yildiz

Dinesh Shetty

Janah Shaya

Affiliations

Soon will be listed here.

Abstract

Suzuki-Miyaura coupling (SMC), a crucial C-C cross-coupling reaction, is still associated with challenges such as high synthetic costs, intricate work-ups, and contamination with homogeneous metal catalysts. Research intensely focuses on strategies to convert homogeneous soluble metal catalysts into insoluble powder solids, promoting heterogeneous catalysis for easy recovery and reuse as well as for exploring greener reaction protocols. Metal-Organic Frameworks (MOFs), recognized for their high surface area, porosity, and presence of transition metals, are increasingly studied for developing heterogeneous SMC. The molecular fence effect, attributed to MOF surface functionalization, helps preventing catalyst deactivation by aggregation, migration, and leaching during catalysis. Recent reports demonstrate the enhanced catalytic activity, selectivity, stability, application scopes, and potential of MOFs in developing greener heterogeneous synthetic methodologies. This review focuses on the catalytic applications of MOFs in SMC reactions, emphasizing developments after 2016. It critically examines the synthesis and incorporation of active metal species into MOFs, focusing on morphology, crystallinity, and dimensionality for catalytic activity induction. MOF catalysts are categorized based on their metal nodes in subsections, with comprehensive discussion on Pd incorporation strategies, catalyst structures, optimal SMC conditions, and application scopes, concluding with insights into challenges and future research directions in this important emerging area of MOF applications.

References

Chen L, Luque R, Li Y . Controllable design of tunable nanostructures inside metal-organic frameworks. Chem Soc Rev. 2017; 46(15):4614-4630. DOI: 10.1039/c6cs00537c. View

Kalaj M, Cohen S . Postsynthetic Modification: An Enabling Technology for the Advancement of Metal-Organic Frameworks. ACS Cent Sci. 2020; 6(7):1046-1057. PMC: 7379093. DOI: 10.1021/acscentsci.0c00690. View

Chen D, Wei L, Yu Y, Zhao L, Sun Q, Han C . Size-Selective Suzuki-Miyaura Coupling Reaction over Ultrafine Pd Nanocatalysts in a Water-Stable Indium-Organic Framework. Inorg Chem. 2022; 61(39):15320-15324. DOI: 10.1021/acs.inorgchem.2c02877. View

Jiao L, Wang Y, Jiang H, Xu Q . Metal-Organic Frameworks as Platforms for Catalytic Applications. Adv Mater. 2017; 30(37):e1703663. DOI: 10.1002/adma.201703663. View

Pascanu V, Hansen P, Bermejo Gomez A, Ayats C, Platero-Prats A, Johansson M . Highly functionalized biaryls via Suzuki-Miyaura cross-coupling catalyzed by Pd@MOF under batch and continuous flow regimes. ChemSusChem. 2014; 8(1):123-30. DOI: 10.1002/cssc.201402858. View

He C, Liang J, Zou Y, Yi J, Huang Y, Cao R . Metal-organic frameworks bonded with metal -heterocyclic carbenes for efficient catalysis. Natl Sci Rev. 2022; 9(6):nwab157. PMC: 9270066. DOI: 10.1093/nsr/nwab157. View

Veisi H, Abrifam M, Ahany Kamangar S, Pirhayati M, Saremi S, Noroozi M . Pd immobilization biguanidine modified Zr-UiO-66 MOF as a reusable heterogeneous catalyst in Suzuki-Miyaura coupling. Sci Rep. 2021; 11(1):21883. PMC: 8575879. DOI: 10.1038/s41598-021-00991-3. View

Han F . Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts. Chem Soc Rev. 2013; 42(12):5270-98. DOI: 10.1039/c3cs35521g. View

Shaya J, Fontaine-Vive F, Michel B, Burger A . Rational Design of Push-Pull Fluorene Dyes: Synthesis and Structure-Photophysics Relationship. Chemistry. 2016; 22(30):10627-37. DOI: 10.1002/chem.201600581. View

10.

Kousik S, Velmathi S . Engineering Metal-Organic Framework Catalysts for C-C and C-X Coupling Reactions: Advances in Reticular Approaches from 2014-2018. Chemistry. 2019; 25(72):16451-16505. DOI: 10.1002/chem.201901987. View

11.

He T, Kong X, Zhou J, Zhao C, Wang K, Wu X . A Practice of Reticular Chemistry: Construction of a Robust Mesoporous Palladium Metal-Organic Framework via Metal Metathesis. J Am Chem Soc. 2021; 143(26):9901-9911. DOI: 10.1021/jacs.1c04077. View

12.

Freund R, Zaremba O, Arnauts G, Ameloot R, Skorupskii G, Dinca M . The Current Status of MOF and COF Applications. Angew Chem Int Ed Engl. 2021; 60(45):23975-24001. DOI: 10.1002/anie.202106259. View

13.

Tanabe K, Cohen S . Postsynthetic modification of metal-organic frameworks--a progress report. Chem Soc Rev. 2010; 40(2):498-519. DOI: 10.1039/c0cs00031k. View

14.

Deng X, Li Z, Garcia H . Visible Light Induced Organic Transformations Using Metal-Organic-Frameworks (MOFs). Chemistry. 2017; 23(47):11189-11209. DOI: 10.1002/chem.201701460. View

15.

Cao Z, Momen R, Tao S, Xiong D, Song Z, Xiao X . Metal-Organic Framework Materials for Electrochemical Supercapacitors. Nanomicro Lett. 2022; 14(1):181. PMC: 9437182. DOI: 10.1007/s40820-022-00910-9. View

16.

Miguel-Casan E, Darawsheh M, Farina-Torres V, Vitorica-Yrezabal I, Andres-Garcia E, Fananas-Mastral M . Heterometallic palladium-iron metal-organic framework as a highly active catalyst for cross-coupling reactions. Chem Sci. 2023; 14(1):179-185. PMC: 9769104. DOI: 10.1039/d2sc05192c. View

17.

Wu Y, Feng X, Zhai Q, Wang H, Jiang H, Ren Y . Metal-Organic Framework Surface Functionalization Enhancing the Activity and Stability of Palladium Nanoparticles for Carbon-Halogen Bond Activation. Inorg Chem. 2022; 61(18):6995-7004. DOI: 10.1021/acs.inorgchem.2c00379. View

18.

Yusuf V, Malek N, Kailasa S . Review on Metal-Organic Framework Classification, Synthetic Approaches, and Influencing Factors: Applications in Energy, Drug Delivery, and Wastewater Treatment. ACS Omega. 2022; 7(49):44507-44531. PMC: 9753116. DOI: 10.1021/acsomega.2c05310. View

19.

Dhakshinamoorthy A, Garcia H . Metal-organic frameworks as solid catalysts for the synthesis of nitrogen-containing heterocycles. Chem Soc Rev. 2014; 43(16):5750-65. DOI: 10.1039/c3cs60442j. View

20.

Nasalevich M, Hendon C, Santaclara J, Svane K, van der Linden B, Veber S . Electronic origins of photocatalytic activity in d0 metal organic frameworks. Sci Rep. 2016; 6:23676. PMC: 4810359. DOI: 10.1038/srep23676. View