Metal–organic frameworks with open metal sites act as efficient heterogeneous catalysts for Knoevenagel condensation and the Chan–Lam coupling reaction

Goswami, Anindita; Dutta, Prantik; Biradha, Kumar

doi:10.1039/d3ce00663h

Cited by 3 publications

(1 citation statement)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, metals can be strategically positioned at speci c sites to normalize the catalytic behaviors and maximize the utilization e ciency of metals. Additionally, the coordinated bonds in MOFs result in rigid structures, further enhancing their stability and performance [43][44][45][46][47][48] . Consequently, under certain conditions, MOFs immobilized catalysts would have similar and even enhanced reactivity and stability over their homogeneous counterparts due to their rigid structure [49][50][51][52][53] .…”

Section: Introductionmentioning

confidence: 99%

Gram-Scale Synthesis of Heterogeneous Cu-MOFs Catalyst with Dual Functionalities for Late-stage Dicarbofunctionalization of Alkenes

Guo,

Dong,

Chen

et al. 2024

Preprint

View full text Add to dashboard Cite

Multifunctional catalysts in organic synthesis are highly attractive, particularly in the construction of complex molecules. Here, we report the first example of heterogeneous Cu-MOFs catalyst with dual functions of photoredox and cross-coupling. IMU-108 can be synthesized on a gram scale from Cu(NO3)2·3H2O and 5-mercaptoisophthalic acid precursors by a simple reflux process. X-ray diffraction results revealed that IMU-108 is constructed from the in-situ bridged S-S bond between the zero-dimension metal-organic polyhedra (MOPs). The inter-polyhedras S-S bonds not only create a rigid geometric structure, but also allow IMU-108 to be bench-stable, while still maintaining excellent catalysis. We demonstrate the capacity of IMU-108 in heterogeneous photoredox-catalyzed cross-coupling of styrenes, α-carbonyl alkyl and bromides with boronic acids to yield various substituted 1,1-diarylalkanes in a single step. The versatility of this method enables late-stage functionalization of complex molecules without the need for de novo synthesis. Moreover, IMU-108 exhibits good recyclability, maintaining its catalytic activity over six consecutive reaction cycles.

show abstract

Section: Introductionmentioning

confidence: 99%

Gram-Scale Synthesis of Heterogeneous Cu-MOFs Catalyst with Dual Functionalities for Late-stage Dicarbofunctionalization of Alkenes

Guo,

Dong,

Chen

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

Zn, Cd and Cu Coordination Polymers for Metronidazole Sensing and for Ullmann and Chan‐Lam Coupling Reactions

Manna,

Boruah,

Natarajan

2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

Five compounds, [Zn(bpe)1/2(BPTA)H2O]·H2O (1); [Zn(bpe)(BPTA)] (2); [Cd(bpe)(BPTA)H2O] (3); [Cd(BPTA)(bpmh)]·2H2O (4); and Cu(BPTA)(bpmh)1.5(H2O)]·H2O (5) were prepared employing 2,5‐bis(prop‐2‐yn‐1‐yloxy)terephthalic acid (2, 5 BPTA) as the primary ligand and 1,2‐di(pyridin‐4‐yl)ethane (4, 4ʹ bpe) (1‐3) and 1,2‐bis(pyridin‐3‐ylmethylene)hydrazine (bpmh) (4‐5) as the secondary ligands. Single crystal studies indicated that the compounds 1, 3 and 5 have two‐dimensional layer structures and compounds 2 and 4 three‐dimensional structures. The luminescence behaviour of the compounds 2 and 3 were explored for the sensing of metronidazole both in aqueouos solution as well as simple paper strips. The Cu compound 5 loses the coordinated water molecule at 100 °C without any structural change, which was examined towards the Lewis acidic character by carrying out the Ullmann type C‐C homocoupling reaction of the aromatic halide compounds. The compounds, 4 and 5, also have the Lewis basic functionality arising out the =N‐N=, aza groups. The bifunctional nature of the MOF was explored towards the Chan‐Lam coupling reaction between phenyl boronic acid and aniline derivatives in the ethanol medium. In both the catalytic reactions, good yields and recyclability were observed. The present studies illustrated the rich diversity that the transition metal containing compounds exhibit in extended framework structures.

show abstract

Deciphering the Knoevenagel condensation: towards a catalyst-free and water-mediated process

Kolagkis,

Serviou,

Stini

et al. 2024

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Metal–organic frameworks with open metal sites act as efficient heterogeneous catalysts for Knoevenagel condensation and the Chan–Lam coupling reaction

Abstract: The acylamide functionalized tetra-carboxylic acid (H4CDA) has been successfully employed for the formation of two robust 3D-MOFs, Cd-CDA-MOF and Cu-CDA-MOF, having open metal sites with two distinct and diverse network...

Cited by 3 publications

References 48 publications

Gram-Scale Synthesis of Heterogeneous Cu-MOFs Catalyst with Dual Functionalities for Late-stage Dicarbofunctionalization of Alkenes

Gram-Scale Synthesis of Heterogeneous Cu-MOFs Catalyst with Dual Functionalities for Late-stage Dicarbofunctionalization of Alkenes

Zn, Cd and Cu Coordination Polymers for Metronidazole Sensing and for Ullmann and Chan‐Lam Coupling Reactions

Deciphering the Knoevenagel condensation: towards a catalyst-free and water-mediated process

Contact Info

Product

Resources

About