Article
Chemistry, Organic
Peng Wang, Ji Yang, Kangkang Sun, Helfried Neumann, Matthias Beller
Summary: The direct palladium-catalyzed selective carbonylative coupling of less reactive aryl chlorides with primary and secondary amines is achieved using a palladium/Xantphos catalyst system and cesium chloride as an additive. This reaction shows high conversion for various aryl chlorides and good functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Dan Li, Li Wei, Chaorong Qi, Wenfang Xiong, Hongjian Liu, Huanfeng Jiang
Summary: A palladium-catalyzed direct carbonylation of aryl bromides with carbon dioxide as the carbonyl source has been developed, providing an efficient route to a variety of aryl carboxylic acids in moderate to high yields. The method has many advantages including the use of a simple palladium catalyst system, wide substrate scope, good functional group tolerance, high yields, and easy scalability.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Xiangyang Xie, Feng Zhang, Huiyu Qin, Xiaoshuang Lu, Bingguang Zhang, Qiaozhen Sun
Summary: A novel macrocyclic bis(N-heterocyclic carbene) precursor was designed and synthesized for the hydrodehalogenation of aryl halides. The synergistic effect of two imida-zoline protons arranged in opposite positions on the macrocycle was found to be closely related to the generation of a small amount of chlorobenzene intermediate product.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Haiwei Zhao, Changhui Lu, Simon Herbert, Wei Zhang, Qilong Shen
Summary: Two protocols for direct difluoromethylation of alkyl bromides and iodides are introduced, utilizing different catalysts and activators. Preliminary mechanistic studies suggest that the synergistic Pd/Cu-catalyzed difluoromethylation of alkyl bromides likely proceeds via a Pd(I)/Pd(III) catalytic cycle.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Csilla Eniko Czegeni, Henrietta Kovacs, Gabor Papp, Agnes Katho, Ferenc Joo
Summary: Anion-exchange resin-supported palladium catalysts are prepared by immobilizing Pd(II) on anion-exchange resins followed by reduction in hydrogen atmosphere. These catalysts exhibit high catalytic activity and selectivity in the dehalogenation of aromatic halides through hydrogen transfer from aqueous sodium formate in water-ionic liquid mixtures under batch conditions and hydrogenation in ethanol under moderate pressure of H2 in a continuous flow microreactor.
INORGANICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Dake Song, Yi Qin, Ying Liu, Jifan Wang, Haijie Yang, Zhonghui Zheng, Feng Xu, Xuefei Bao, Guoliang Chen
Summary: The immobilization of ciprofloxacin on chloromethyl polystyrene resin as a recyclable ligand for copper-catalyzed coupling reactions of (hetero)aryl halides and amines provides excellent results. The ligand is easily recovered and reused without loss of catalytic ability, and is environmentally friendly with no detectable ciprofloxacin in the reaction solution. Important structural units for the pharmaceutical and chemical industries can be assembled using this method.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Baptiste Picard, Takahide Fukuyama, Ilhyong Ryu
Summary: An improved carbonylation method for amide bond formation between aryl iodides and aromatic amines is presented, which does not require a phosphine ligand unlike conventional Pd catalysis. The catalyst system consists of bis(dibenzylideneacetone)palladium (0.5 mol %) and DBU (10 mol %). This method allows the synthesis of various aromatic amides and can be scaled to gram order synthesis under low carbon monoxide pressure.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Liangliang Tong, Xinluo Song, Yuxin Jiang, Bangyao Zhao, Yafeng Li
Summary: In this study, ultrafine palladium nanoparticles were successfully immobilized into the metal-organic framework UiO-66 by impregnation reduction method. The resulting Pd@UiO-66 catalyst showed excellent activity and stability in catalytic transfer hydrogenation of aryl and heteroaryl halides using ammonium formate as the hydrogen donor.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2022)
Article
Engineering, Environmental
Ling Tan, Meizi Liu, Lixian Wang, Guoping Zhao, Yanfei Zhang
Summary: A novel semi-quantitative method using flow cytometry analysis of side scatter intensity has been proposed to measure the adsorption capacity of individual cells to Pd(II). This method enables high-throughput screening of specific peptides/proteins with high Pd(II) affinity.
JOURNAL OF HAZARDOUS MATERIALS
(2024)
Article
Chemistry, Inorganic & Nuclear
Michal Kolodziejski, Aidan J. Brock, Gracjan Kurpik, Anna Walczak, Feng Li, Jack K. Clegg, Artur R. Stefankiewicz
Summary: A variety of morphologically distinct metallosupramolecular Cu(II) and Pd(II) complexes have been constructed based on the tritopic ligand H3L, showing different coordination assemblies with either macrocyclic or polymeric structures and distinct catalytic activity in the Suzuki-Miyaura cross-coupling reaction through control of reaction conditions.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Peng Xue, Liubo Li, Niankai Fu
Summary: This paper reports an electrocatalytic method for esterification of aryl halides using a combination of iron and nickel electrocatalysis. The reaction involves anodic iron-catalyzed oxidation of carbazates to produce alkoxycarbonyl radicals. Subsequently, the carbon-centered radicals undergo nickel catalysis driven by cathodic reduction to form radical coupling products. Mechanistic data demonstrate that arylnickel(II) species are crucial intermediates for the desired carbon-carbon bond formation.
Article
Chemistry, Physical
Adrian Tlahuext-Aca, Sarah Yunmi Lee, Shu Sakamoto, John F. Hartwig
Summary: A new method for the direct catalytic arylation of simple arenes using aryl bromides is described. The method does not rely on directing groups and instead utilizes a synergistic catalytic cycle involving phosphine-ligated silver complexes and palladium catalysts. Mechanistic experiments indicate that cleavage of the C-H bond by silver is the rate-determining step in the catalytic cycle.
Article
Chemistry, Organic
Adesh Kumar Singh, Rapelly Venkatesh, Vimlesh Kumar Kanaujiya, Varsha Tiwari, Jeyakumar Kandasamy
Summary: An efficient method for the synthesis of C-1 aryl enones from aryl iodides and glycal enones through palladium-catalyzed cross-coupling reactions under ligand-free conditions was developed. This method is applicable to a wide range of aryl iodides with different electron-donating and withdrawing groups, and can be carried out under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Matz Liebel, Irene Calderon, Nicolas Pazos-Perez, Niek F. van Hulst, Ramon A. Alvarez-Puebla
Summary: Large-scale SERS particle screening (LSSPS) is a fast multiplexed widefield screening approach that quantifies both Raman and Rayleigh scattering simultaneously, allowing for direct quantification of the fraction of SERS-active particles and unprecedented correlation of SERS activity with particle size.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Editorial Material
Chemistry, Multidisciplinary
David K. Leonard, Pavel Ryabchuk, Muhammad Anwar, Sarim Dastgir, Kathrin Junge, Matthias Beller
Summary: The researchers developed a nickel-based catalyst supported on titania for hydrodehalogenation reactions. By using design of experiments, they demonstrated the catalyst's effectiveness in removing various halogens from different substrates. Additionally, the catalyst system showed practicality in dehalogenating environmentally hazardous polyhalogenated substrates.
Article
Chemistry, Organic
Mingyeong Jang, Taeho Lim, Byoung Yong Park, Min Su Han
Summary: This study presents a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds, using tetrahydroxydiboron as the reductant. The reaction can be completed within 5 minutes at room temperature and selectively converts nitroarenes with sensitive functional groups into anilines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Analytical
Namgeol Lee, Soyeon Yoo, Youngkeun Lee, Min Su Han
Summary: The Mn2BPMP complex exhibits high intrinsic peroxidase-like activity at pH 7, which is higher than most small-molecule-based peroxidase mimics. It also shows high reproducibility. The peroxidase-like activity is significantly boosted by adenosine mono/diphosphate (AMP and ADP). A colorimetric one-pot assay system was established based on the enzyme cascade reaction between analyte oxidase and ADP-boosted Mn2BPMP, enabling rapid detection of glucose and cholesterol.
Article
Chemistry, Analytical
Mincheol Jang, Min Su Han
Summary: 19F NMR spectroscopy is a noninvasive analytical technique that helps understand complex natural phenomena at the atomic level. However, current referencing techniques for 1H NMR have limitations when applied to heteronuclear NMR. In this study, a new strategy using an internal standard method is proposed to improve the consistency of 19F NMR referencing. The results show that this strategy is robust and reproducible, allowing reliable analyses of multiple analytes simultaneously.
ANALYTICAL CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Seungyoon Kang, Byoung Yong Park, Dohyun Moon, Min Su Han
Summary: Hetero-dinuclear synergic catalysis is a promising approach for improving catalytic performance, but the design principles for the metal complex are still not well understood. In this study, we used a high-throughput approach to obtain a new hetero-dinuclear synergistic metal complex for H2O2 activation. The lead complex (L3-(Ni, Co)) was derived from 1152 combinations of metal complex candidates and showed the highest peroxidase activity, demonstrating clear hetero-bimetallic synergism.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Jinyoung Oh, Chanhyuk Min, Daeho Park, Min Su Han
Summary: Simultaneous detection has been achieved using dual responsive probes, which can help understand complex physiological processes and accurately diagnose diseases. A new detection platform, using a linkage between versatile oligonucleotide probes and small-molecule chemosensors, has been developed to expand the applicable scaffold and detectable target.
Article
Materials Science, Multidisciplinary
Suji Lee, Jinyoung Oh, Min Su Han
Summary: In this study, a photoactivatable, artificial peroxidase system based on a photocaging approach was developed. The raw peroxidase activity of the system could be restored by light irradiation, and the activation degree could be tuned by varying the irradiation time and/or light intensity. This system was further utilized for light-controlled hydrogelation, allowing for the preparation of hydrogels with desired shapes and regulated mechanical properties depending on the light exposure time.
ACS APPLIED POLYMER MATERIALS
(2022)
Article
Chemistry, Applied
Byoung Yong Park, Min Su Han
Summary: In this study, an effective synthesis of a copper nanoparticle-graphitic carbon nitride (g-C3N4) composite was presented for the selective transfer semihydrogenation of alkynes. A fluorescence-based high-throughput screening method was used to identify the most synergistic support for copper nanoparticles. The Cu(OAc)(2)/g-C3N4 system achieved a significant increase in turnover frequency compared to the copper nanoparticle catalyst alone, and showed high selectivity and yield in the reduction of alkynes to (Z)-alkenes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Analytical
Hyuna Lee, Suji Lee, Min Su Han
Summary: pH monitoring is important for surveilling human health, industries, and the environment. However, there is a scarcity of fluorescent probes capable of sensing alkaline regions. This study proposes turn-on-type fluorescent probes derived from bis(HBX) for detecting alkaline pHs. These probes exhibit strong fluorescence intensity and color changes at alkaline pHs, and possess good photostability, reversibility, and anti-interference towards pH variations.
Article
Chemistry, Organic
Min Sik Eom, Byoung Yong Park, Seungyoon Kang, Min Su Han
Summary: A salicylimine-based fluorophore, Di-OH, was developed that selectively responded to boric acid over boronic acid. It was further applied for screening the conversion rate of a chemical reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Hyungjin Cho, Suji Lee, Min Su Han
Summary: This study prepared a library of 238 different bDABs through combinatorial synthesis and identified four bDABs with promising pH-sensitive ratiometric fluorescence responses. These bDABs were found to be suitable for detecting basic pHs even in extremely basic environments, with high stability, anti-interference, and reversibility under various pH conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Soyeon Yoo, Sudeok Kim, Sangyeon Jeon, Min Su Han
Summary: A new peroxidase substrate MNDH was developed in this study, which showed quantitative fluorescence changes with respect to H2O2 concentration in the presence of horseradish peroxidase and no changes in fluorescence caused by over-oxidation in the presence of excess H2O2. Moreover, MNDH exhibited good thermo- and photostability and could be operated over a wide pH range.
Article
Chemistry, Multidisciplinary
Suji Lee, Min Su Han
Summary: We described an analyte-activatable artificial peroxidase system by caging a dimanganese complex with an analyte-reactive trigger. This system allowed adjustments of the detection target based on the trigger and detection modes, such as fluorescence and colorimetric. It was successfully applied to a versatile enzyme assay for leucine aminopeptidase and gamma-glutamyl transpeptidase based on spectrophotometric change induced from the oxidation of the peroxidase substrate by analyte-triggered peroxidase-like activity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jihoon Kim, Jinyoung Oh, Min Su Han
Summary: A ratiometric and selective hydrogen sulfide detection probe was developed based on the metal ion displacement mechanism, showing rapid response and high sensitivity with a detection limit of 70 nM. The probe exhibited unchanged monomer emission as an internal reference and enhanced excimer emission with the addition of H2S. The method was successfully applied for detecting H2S in human serum without interference from biological molecules.
Article
Chemistry, Organic
Hyungwoo Hahm, Jiyun Kim, Jeong Yup Ryoo, Min Su Han, Sukwon Hong
Summary: A metal-free photoredox-catalyzed carbocarboxylation method has been developed for the synthesis of gamma-aminobutyric ester derivatives, with yields up to 91%. The method is effective for a variety of substituted styrenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Byoung Yong Park, Taeho Lim, Min Su Han
Summary: The study developed a simple, effective, and practical method for (Z)-selective semihydrogenation of alkynes, achieving up to 99% yield by generating a copper nanocatalyst in situ simply by adding ammonia borane to an ethanol solution of copper sulfate. The method eliminates catalyst preparation and serves as an alternative to the conventional Lindlar catalyst.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
