A tertiary phosphine oxide ligand-based recyclable system for the Suzuki–Miyaura and Negishi reactions: evidence for pseudo-homogeneous catalysis

King, Andrew Kevin; Brar, Aneelman; Findlater, Michael

doi:10.1039/d2cy01734b

Cited by 8 publications

(6 citation statements)

References 31 publications

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“…We suspect the proposal to mix these compounds arises as an artifact of making a combinatorial array (phactor) out of the popular Pd complex and ligand choices from the literature (ChatGPT). Nonetheless, the observation that this “cocktail” of ligands was the most productive result could be supported by related reports of “cocktail” catalysis in the Buchwald–Hartwig coupling. − …”

Section: Resultssupporting

confidence: 59%

Designing Chemical Reaction Arrays Using Phactor and ChatGPT

Mahjour,

Hoffstadt,

Cernak

2023

Org. Process Res. Dev.

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High-throughput experimentation is a common practice in the optimization of chemical synthesis. Chemists design reaction arrays to optimize the yield of couplings between building blocks. Popular reactions used in pharmaceutical research include the amide coupling, Suzuki coupling, and Buchwald–Hartwig coupling. We show how the artificial intelligence (AI) language model ChatGPT can automatically formulate reaction arrays for these common reactions based on the literature corpus it was trained on. Critically, we showcase how ChatGPT results can be directly translated into inputs for the management software phactor, which enables automated execution and analysis of assays. This workflow is experimentally demonstrated, with modest to excellent yields of products obtained in each instance on the first attempt.

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Section: Resultssupporting

confidence: 59%

Designing Chemical Reaction Arrays Using Phactor and ChatGPT

Mahjour,

Hoffstadt,

Cernak

2023

Org. Process Res. Dev.

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“…Thus, the bound SiAu 5 cluster lowers the activation energy barrier for CO oxidation, and the reaction occurs more readily compared with the Au 6 cluster process. In addition, we also noted that the reactivity and catalytical effects are also affected by supports for different metal oxide surfaces [ 5 , 9 , 20 ]. Moreover, experimental investigations are important for understanding CO oxidation on SiAu n clusters.…”

Section: Resultsmentioning

confidence: 99%

“…Metal clusters have long been extensively studied due to their unique optical, electronic, and mechanical properties, as well as their wide range of applications in catalysts [ 1 , 2 , 3 , 4 ]. Among the various types of metal clusters, Au clusters have attracted much attention as size-tunable prototypes, because they have been shown to have significant catalytic activity [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Chen et al [ 20 ] showed that Au loading and the Au particle size have significant effects on the generation of methanol and CO; with an increase in the Au loading/Au particle size, the generation activity (Au-mass-normalized reaction rate, TOF) for methanol and CO decreases, while the selectivity for methanol generation increases.…”

Section: Introductionmentioning

confidence: 99%

Mechanisms for Catalytic CO Oxidation on SiAun (n = 1–5) Cluster

Zhang

Ren

2023

Molecules

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Significant progress has been made in understanding the reactivity and catalytic activity of gas-phase and loaded gold clusters for CO oxidation. However, little research has focused on mixed silicon/gold clusters (SiAun) for CO oxidation. In the present work, we performed density function theory (DFT) calculations for a SiAun (n = 1–5) cluster at the CAM-B3LYP/aug-cc-pVDZ-PP level and investigated the effects on the reactivity and catalytic activity of the SiAun cluster for CO oxidation. The calculated results show that the effect is very low for the activation barriers for the formation of OOCO intermediates on SiAu clusters, SiAu3 clusters, and SiAu5 clusters in the catalytic oxidation of CO and the activation energy barriers for the formation of OCO intermediates on OSiAu3, OSiAu4, and OSiAu5. Our calculations show that, compared with the conventional small Au cluster, the incorporation of Si enhances the catalytic performance towards CO oxidation.

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“…Therefore, to obtain a good yield of the desired cross-coupled product, the reaction was studied by varying different reaction parameters. Literature reports suggest that the solvent system plays a vital role in the SMCC reaction. ,, Hence using the same amount of substrate, catalyst, and base, the reaction was performed in different organic solvents at room temperature. The solvent optimization graph depicted in Figure S7 suggested that CH 3 OH was more suitable in comparison to other solvents like EtOH, CH 3 CN, and isopropanol for this particular reaction under these conditions.…”

Section: Catalytic Studymentioning

confidence: 99%

Low-Palladium-Content Iron(III) Nanocatalyst Supported on Zeolite-NaY for C–Cl Bond Activation

Bora,

Hazarika,

Gour

et al. 2023

ACS Appl. Nano Mater.

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A heterogeneous nanocatalyst comprising palladium (Pd/PdO) and iron(III) oxide (Fe 2 O 3 ) in the dimension of 1−4 nm was synthesized using sodium-exchanged zeolite-Y or zeolite-NaY [a type of faujasite (FAU) zeolite having an aluminosilicate framework with a general formula of (Na 2 ) 3.5 [Al 7 Si 17 O 48 ]•32H 2 O] as a support matrix. The catalyst was investigated as a true heterogeneous catalyst for activation of the robust C−Cl bond of aryl chlorides in the Suzuki−Miyaura cross-coupling (SMCC) reaction. The catalyst with very low Pd loading (0.0037 mol %) exhibited high reactivity in the SMCC reaction with various derivatives of aryl chlorides (Ar−Cl). Biaryl products were obtained with up to a 92% yield, high selectivity, and a good turnover number with this Pd/PdO−Fe 2 O 3 -Y catalyst. The catalyst exhibited good thermal stability and was highly recyclable. The reaction was found to be reliant on various parameters such as solvent system, temperature, time, and catalyst amount. A small aliquot of water (H 2 O) mixed with methanol (CH 3 OH) dramatically brought a substantial improvement in the product yield of the desired biaryl product. The role of zeolite-NaY was also investigated by comparing the results with various other synthesized catalysts. Different experimental studies indicated that the surface hydroxyl (−OH) groups of zeolite-NaY, modification of basic sites, and the ability to influence the reduction temperature of iron (Fe) and palladium (Pd) influenced the catalytic performance of the synthesized catalyst. The impact of Fe on the electronic structure and reactivity of Pd was analyzed through a density functional theory calculation. This study provided strong evidence for creation of a negative (−ve) charge on Pd with an increasing amount of Fe content and thereby favored the in situ transformation of Pd(II) to Pd(0) as required in the activation of the C−Cl bond.

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A tertiary phosphine oxide ligand-based recyclable system for the Suzuki–Miyaura and Negishi reactions: evidence for pseudo-homogeneous catalysis

Abstract: A recoverable catalyst system has been developed and its application in both Suzuki-Miyaura and Negishi coupling reactions has been demonstrated. We have also investigated the nature of the active catalyst...

Cited by 8 publications

References 31 publications

Designing Chemical Reaction Arrays Using Phactor and ChatGPT

Designing Chemical Reaction Arrays Using Phactor and ChatGPT

Mechanisms for Catalytic CO Oxidation on SiAun (n = 1–5) Cluster

Low-Palladium-Content Iron(III) Nanocatalyst Supported on Zeolite-NaY for C–Cl Bond Activation

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