Amidation via ligand-free direct oxidative C(sp3)-H/NH coupling with Cu-CPO-27 metal-organic framework as a recyclable heterogeneous catalyst

Hoang, Thanh Truc Nguyen; Nguyen, Hien-Anh Thi; Le, Tien Thi Thuy; Le, Dung Tien; Truong, Thanh; Phan, Nam T. S.

doi:10.1016/j.tet.2016.10.059

Cited by 11 publications

(7 citation statements)

References 81 publications

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“…Next, the reaction should be carried out at the temperatures around 100 o C with reference to the previous researches. [7][8]19 Hence, the effect of temperature on reaction was investigated from 80 o C to 140 o C (entries [13][14][15]. No or only trace amount of the product was detected when the reaction was carried out under 120 o C (entries [13][14].…”

Section: Resultsmentioning

confidence: 99%

“…7 Cheng and coworkers implemented the same transformation deploying 10 mol% Cu(acac)2 complex as catalyst. 8 While our previous method using Cu-CPO-27 used 7.5% mol of the catalyst, 19 the employment of Cu2(BDC)2(DABCO) catalyst not only did not require additional ligands but also replaced Cu-CPO-27 by a cheaper heterogeneous catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…[15][16][17][18] In this manuscript, we would like to illustrate an efficient access to N-cyclohexylbenzamide via direct oxidative C-N coupling reaction. To the best of our knowledge, this synthetic route was previously conducted under Cu-CPO-27 as a heterogeneous catalyst, 19 but the material for synthesizing this MOF is very expensive. Therefore, in this study, Cu2(BDC)2DABCO was investigated as an alternative due to its much cheaper cost of starting materials.…”

Section: Introductionmentioning

confidence: 99%

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Cu2(BDC)2DABCO as an efficient heterogeneous catalyst for the oxidative C-N coupling reaction between amides and unactivated alkanes

Anh¹,

Thuy²,

Thai³

et al. 2020

Vietnam j. catal. adsorp.

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A copper-organic framework Cu2(BDC)2DABCO was synthesized, and used as a recyclable heterogeneous catalyst for C-N coupling reaction between benzamide and cyclohexane. 94% yield of N-cyclohexylbenzamide was achieved under the optimized condition. The copper-organic framework catalyst was truly heterogeneous and could be used at least 4 cycles without degradation of catalytic performance. To the best of our knowledge, the amidation of unactivated alkanes by benzamides via direct oxidative C-N coupling was previously performed under heterogeneous catalysis conditions but very rare.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cu2(BDC)2DABCO as an efficient heterogeneous catalyst for the oxidative C-N coupling reaction between amides and unactivated alkanes

Anh¹,

Thuy²,

Thai³

et al. 2020

Vietnam j. catal. adsorp.

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“…[36] Zn-MOF-74 is intensively studied for gas storage [36] and separation [37] as well as in catalysis. [38][39][40][41][42][43][44][45] It has a3 Dh oneycomblike framework with 1D channels of ca. 11 , [46] built from organic linkers on the edges and ZnO 6 at the corners.…”

Section: Introductionmentioning

confidence: 99%

“…It is focused on a material, which is recognised as the MOF with the highest density of open metal sites, namely [Zn 2 (dobdc)(H 2 O) 2 ] (H 4 dobdc=2,5‐dioxido‐1,4‐benzenedicarboxylic acid), known as Zn‐MOF‐74 [36] . Zn‐MOF‐74 is intensively studied for gas storage [36] and separation [37] as well as in catalysis [38–45] . It has a 3D honeycomb‐like framework with 1D channels of ca.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Gheorghe

Strudwick

Dawson

et al. 2020

Chemistry A European J

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The synthesis of chiral metal-organic frameworks (MOFs)i sh ighly relevant for asymmetric heterogenous catalysis, yet very challenging. Chiral MOFsw ith MOF-74 topology were synthesised by using post-synthetic modification with proline. Vibrational circular dichroism studies demonstrate that prolinei st he source of chirality.T he solvents used in the synthesis play ak ey role in tuning the loading of proline and its interaction with the MOF-74 framework. In N,N'-dimethylformamide, proline coordinates monodentate to the Zn 2 + ions withint he MOF-74 framework, whereasi ti s only weakly bound to the frameworkw hen using methanol as solvent. Introducing chirality within the MOF-74f ramework also leads to the formation of defects, with both the organic linkera nd metal ions missing from the framework. The formationo fd efects combined with the coordination of DMF and prolinew ithin the framework leads to ap ore blockinge ffect. This is confirmed by adsorption studies and testingo ft he chiral MOFs in the asymmetric aldol reaction betweenacetone and para-nitrobenzaldehyde.

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Catalytic Alkane Amidation and Related Reactions

Nesterov

Frija

Pombeiro

et al. 2018

Alkane Functionalization

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Amidation via ligand-free direct oxidative C(sp3)-H/NH coupling with Cu-CPO-27 metal-organic framework as a recyclable heterogeneous catalyst

Cited by 11 publications

References 81 publications

Cu<sub>2</sub>(BDC)<sub>2</sub>DABCO as an efficient heterogeneous catalyst for the oxidative C-N coupling reaction between amides and unactivated alkanes

Cu<sub>2</sub>(BDC)<sub>2</sub>DABCO as an efficient heterogeneous catalyst for the oxidative C-N coupling reaction between amides and unactivated alkanes

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Catalytic Alkane Amidation and Related Reactions

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