Synthesis of anion conducting polymer electrolyte membranes by Pd-Catalyzed Buchwald-Hartwig Amination coupling reaction

Pagels, Michael K.; Walgama, Ramali C.; Bush, Nancy G.; Bae, Chulsung

doi:10.1016/j.tet.2019.05.048

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…41 Thus, spirocyclic piperizinium is a potential candidate, as the tertiary amine could act as a linker (11, 12, and 14 in Scheme 4). 43 However, faster degradation than 10 was detected, and a plausible pathway is shown in Scheme 5. It is proposed that the extra nitrogen atom accelerated the ring-opening Hofmann elimination, and the resultant enamine intermediate hydrolyzed thereafter (Scheme 5).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Degradation of Organic Cations under Alkaline Conditions

et al. 2020

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Understanding the degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability within KOH/CD 3 OH solution at 80 °C. Herein, we are using the protocol to compare 26 model compounds, including benzylammonium, tetraalkylammonium, spirocyclicammonium, imidazolium, benzimidazolium, triazolium, pyridinium, guanidinium, and phosphonium cations. The goal is not only to evaluate their degradation rate, but also to identify their degradation pathways and lead to the advancement of cations with improved alkaline stabilities.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Degradation of Organic Cations under Alkaline Conditions

et al. 2020

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“…Buchwald-Hartwig amination reaction is one of the research hot points in the field of coupling reaction of C-N bond catalyzed by Pd [1][2][3][4]. In order to improve the yield of Buchwald-Hartwig cross coupling reaction, researchers have been committed to improving reaction conditions such as ligands and additives in the reaction [5][6][7][8]. However, the current Buchwald-Hartwig cross coupling reaction is obviously facing corresponding shortcomings.…”

Section: Introductionmentioning

confidence: 99%

OCS-TGBM: Intelligent Analysis of Organic Chemical Synthesis Based on Topological Data Analysis and LightGBM

Guo,

Peng,

et al. 2023

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Organic synthesis has been widely used in drug discovery and development. The intelligent prediction and analysis of high-throughput coupling reaction yield is one of the important and challenging research hotspots in the field of organic synthesis. However, the existing methods focus on intelligent prediction rather than study and interpret the internal relationship between reaction conditions and yield. For tackling this problem, an intelligent analysis organic chemical synthesis model by combining topological data analysis (TDA) and Light Gradient Boosting Machine (LightGBM), named OCS-TGBM, is proposed to deeply explore the internal relationship between reaction conditions and yield, and obtain high-yield reaction conditions and combinations. In order to further enhance the performance of the OCS-TGBM model, a stratified diversity sampling strategy is introduced. Experimental results show that the OCS-TGBM model is superior to other methods in analyzing and predicting the reaction performance of high-throughput organic chemical synthesis. And it provides intelligent assistance for the optimal design of the reaction system and the evaluation of reaction conditions, thus greatly accelerating the process of the drug discovery and development.

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Copper‐NHC Based Ullmann Catalysis in Water for Selective N‐Arylation of 3‐Aminophenols

et al. 2020

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Studies of environmentally benign catalytic methods are of great value in modern chemical synthesis, especially the chemo‐selective construction of chemical bonds under green conditions. This work elucidates such preferential synthesis of C−N bond over C−O bond via selective N‐arylation of 3‐aminophenols using 1,3‐bis‐[2‐hydroxyphenyl] imidazolium chloride (IHPHCl) and copper iodide as catalyst (1 mol %) in aqueous medium. Presence of chelating group (−OH) on IHPHCl enhances N‐selectivity. Overall this is a simple and green method for selective N‐arylation of 3‐aminophenols with good substrate scope and yields (60–88 %). GC‐MS, HRMS and other spectroscopic techniques were utilised in detailing the kinetics and mechanistic aspects.

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Synthesis of anion conducting polymer electrolyte membranes by Pd-Catalyzed Buchwald-Hartwig Amination coupling reaction

Cited by 4 publications

References 31 publications

Degradation of Organic Cations under Alkaline Conditions

Degradation of Organic Cations under Alkaline Conditions

OCS-TGBM: Intelligent Analysis of Organic Chemical Synthesis Based on Topological Data Analysis and LightGBM

Copper‐NHC Based Ullmann Catalysis in Water for Selective N‐Arylation of 3‐Aminophenols

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