Article
Chemistry, Organic
Lalita Tanwar, Jonas Boergel, Johannes Lehmann, Tobias Ritter
Summary: Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. The strategy presented here allows for selective C-H iodination of (hetero)arenes with a broad functional group tolerance, showcasing the utility and differentiation from other iodination methods for a set of carboarenes and heteroarenes.
Article
Chemistry, Multidisciplinary
Jay S. Wright, Liam S. Sharninghausen, Sean Preshlock, Allen F. Brooks, Melanie S. Sanford, Peter J. H. Scott
Summary: This article presents a novel method for the meta-selective C-H radiofluorination of (hetero)arene substrates. The process can be conducted on a benchtop without the need for Schlenk or glovebox techniques, resulting in higher yields and purity of the products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Marc Magre, Shengyang Ni, Josep Cornella
Summary: This review evaluates and summarizes the progress in the synthesis of highly fluorinated aryl-S-VI compounds at all levels, discussing synthetic strategies, reactivity, the advantages and disadvantages of the synthetic procedures, the proposed mechanisms, and the potential upcoming opportunities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chunyang Hu, Fangming Chen, Guo-Ping Lu, Wen-Bin Yi
Summary: A new, stable, and scalable reagent, PhthSCF(2)D, has been developed for deuteriodifluoromethylthiolation, which can be applied in both photocatalytic radical and electrophilic reactions.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Wenjie Jiang, Fangjun Shao, Jiaxu Cheng, Fandong Ma, Zhongzhe Wei, Xing Zhong, Hong Wang, Jianguo Wang
Summary: Deuterium-labeled aromatics are crucial for the production of fine chemicals. A Pt/Ca12Al14Ox catalyst with complex valence was synthesized and successfully used for the deuteration of toluene using inexpensive D2O. It exhibited high deuteration efficiency, achieving 96% deuteration in just 4 hours, surpassing the performance of commonly used Pt/C catalyst. The catalyst can also be reused up to 16 times, showing good stability.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Gaijun Xue, Fukai Xie, Hongliang Liang, Guoliang Chen, Wen Dai
Summary: In this study, a protocol for the direct synthesis of nitriles via copper-catalyzed oxidative cleavage and cyanation of C-C bonds in various multicarbon alkyl-substituted (hetero)arenes is reported. Mechanistic studies reveal the involvement of a tandem oxidative process in this transformation.
Review
Chemistry, Multidisciplinary
Zhaohong Liu, Paramasivam Sivaguru, Yongquan Ning, Yong Wu, Xihe Bi
Summary: (Hetero)arenes are crucial in pharmaceuticals, materials science, and synthetic chemistry. The controllable modification of these compounds through peripheral and skeletal editing is a challenging goal. This review focuses on the skeletal editing reactions of (hetero)arenes using carbenes, discussing mechanistic considerations and applications in natural product syntheses.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Medicinal
Yuanyuan Shi, Jean Dinh, Robert Pelletier, Brianne Raccor, Naeem Yusuff, Adam Morgan, Scott Harbeson, Vinita Uttamsingh, Rheem Totah
Summary: Strategically replacing hydrogen with deuterium at sites of metabolism in small molecule drugs can alter drug clearance and enhance clinical safety. Incorporating deuterium at specific sites in bupropion may reduce epimerization, slow metabolism, and decrease the formation of toxic metabolites. Experimental results demonstrate that deuterated bupropion analogues exhibit decreased racemization and formation of certain metabolites in vitro. Selective deuterium substitution at metabolic sites in bupropion has the potential to provide a drug with simplified pharmacokinetics, reduced toxicity, and improved tolerability.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Review
Chemistry, Organic
Liming Cao, Yu Hua, Hong-Gang Cheng, Qianghui Zhou
Summary: Palladium-catalyzed C-H activation has emerged as a versatile strategy for constructing valuable scaffolds, particularly through palladacyclopentane-type intermediates for C-H hetero-functionalization of arenes. Significant progress has been made in this field over the past decade, both in research and applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Stefan Dix, Paul Golz, Jonas R. Schmid, Sebastian Riedel, Matthew N. Hopkinson
Summary: The introduction of bis(trifluoromethyl)peroxide as a practical trifluoromethoxylating reagent opens up a new and efficient method for preparing trifluoromethoxylated arenes. This reagent, easily accessible from inexpensive bulk chemicals, allows for the preparation of trifluoromethoxylated arenes in good yields under mild conditions directly from unactivated aromatics using visible light photoredox or TEMPO catalysis. Additionally, TEMPO catalysis enables the one-step synthesis of valuable pyridine derivatives, simplifying the synthetic process.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Linwei Huang, Wei Liu, Liang-Liang Zhao, Zengyu Zhang, Xiaoyu Yan
Summary: This study investigated the t-BuOK-catalyzed H/D exchange reaction of difluoromethylarenes in DMSO-d(6) solution, which showed excellent deuterium incorporation at the difluoromethyl group. Additionally, the impact of a trace amount of D2O in the DMSO-d(6) solution on the deuteration reaction was also examined.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shiv Shankar Gupta, Manisha, Rakesh Kumar, Ankit Kumar Dhiman, Upendra Sharma
Summary: A regioselective para-C-H halogenation method using SEAr type reaction for N-pyrimidyl (hetero)aromatics has been developed, with wide applicability and high yields for bromination, iodination, and challenging chlorination. The pyrimidyl group acts as a reactivity tuner controlling the regioselectivity, and DFT studies support the observed para-selectivity. Late-stage C-H bromination was also demonstrated on drug/natural molecules to showcase the protocol's applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jagriti Chaturvedi, Chabush Haldar, Ranjana Bisht, Gajanan Pandey, Buddhadeb Chattopadhyay
Summary: An electrostatically directed meta borylation method allows for highly selective borylation reactions on various substrates. This method avoids the need to synthesize complex ligands/templates and can be conducted under milder conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Murugan Subaramanian, Ganesan Sivakumar, Vinod G. Landge, Rohit Kumar, Kishore Natte, Rajenahally V. Jagadeesh, Ekambaram Balaraman
Summary: The catalytic utilization of methanol in organic synthesis and energy technologies is important for fundamental research and industrial applications. Methanol can be used as a hydrogen donor and solvent for selective reduction and deuteration reactions, as well as a source of methyl groups for the synthesis of N-methylated products. This Ru-based catalytic strategy is convenient for the deuteration process and gram-scale synthesis of deuterated pharmaceuticals.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Lin Wang, Yong Xia, Volker Derdau, Armido Studer
Summary: This study presents a metal-free method for the remote deuterium incorporation into aliphatic C-H bonds in various amides, using inexpensive heavy water as the deuterium source. The method demonstrates high site-selectivity and potential utility for deuterium incorporation into natural product derivatives and drugs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Abdallah I. M. Rabee, Dan Zhao, Sebastian Cisneros, Carsten R. Kreyenschulte, Vita Kondratenko, Stephan Bartling, Christoph Kubis, Evgenii Kondratenko, Angelika Brueckner, Jabor Rabeah
Summary: Gold-based catalysts with low gold loading supported on TiO2 and ZrO2 were synthesized and characterized. The Au/TiO2 catalyst showed higher activity than Au/ZrO2 at 250℃, with different reaction mechanisms involved.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2023)
Article
Chemistry, Multidisciplinary
Felix Unglaube, Hanan Atia, Stephan Bartling, Carsten R. Kreyenschulte, Esteban Mejia
Summary: This study utilized rice husk as a support and synthesized a catalyst by impregnating nickel onto the rice husk, which showed excellent activity and selectivity towards anti-Markovnikov alcohols. The catalyst acted as both Bronsted acid and solid Lewis acid, as well as a hydrogenation catalyst.
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Physical
Georg Schnell, Christian Polley, Robert Thomas, Stephan Bartling, Johannes Wagner, Armin Springer, Hermann Seitz
Summary: In this study, the researchers used a customized instrument to investigate the lateral adhesion forces on femtosecond laser-structured surfaces. They found that the droplet motion was significantly influenced by the chemical and topographical surface features. The droplet mobility was classified into static, transfer, and kinetic regimes, which is crucial for designing surfaces with extreme wetting characteristics.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Chemistry, Physical
Nils Ortner, Dan Zhao, Hesham Mena, Jana Weiss, Henrik Lund, Stephan Bartling, Sebastian Wohlrab, Udo Armbruster, Evgenii V. Kondratenko
Summary: CO2 hydrogenation to methanol proceeds through two parallel reactions, with CH3OH decomposition mainly contributing to the loss of CH3OH selectivity. The decomposition is accelerated by H2O but negatively affected by H2 and rising total pressure. The reaction occurs on separate sites from CH3OH synthesis and can be suppressed by site saturation. This concept provides fundamental insights for catalyst design and reaction optimization for selective CH3OH synthesis.
Article
Engineering, Environmental
Yuming Li, Qiyang Zhang, Shuting Fu, Vita A. Kondratenko, Tatiana Otroshchenko, Stephan Bartling, Yaoyuan Zhang, Anna Zanina, Yajun Wang, Guoqing Cui, Mingxia Zhou, Zhen Zhao, Chunming Xu, Guiyuan Jiang, Evgenii V. Kondratenko
Summary: In this study, it was found that CoOx species on the catalyst support transform into Co-0 species, which is crucial for the selective dehydrogenation of propane to propylene. The transformation of CoOx is influenced by metal-oxide-support interactions and the presence of defective OH groups in ZSM-5-type zeolites. The presence of CoOx is also shown to inhibit coke formation and the developed Co/S-1 catalyst exhibited high activity.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Physical
Zupeng Chen, Carolin Amber Martina Stein, Ruiyang Qu, Nils Rockstroh, Stephan Bartling, Jana Weiss, Christoph Kubis, Kathrin Junge, Henrik Junge, Matthias Beller
Summary: In this study, effective palladium catalysts with tunable metal-support interaction and electronic properties were synthesized. The optimal system consisted of highly dispersed Pd nano-particles on carbon nitride. It exhibited a significantly increased rate of gas formation compared to the benchmark catalyst (Pd/C). The state-of-the-art catalyst showed superior long-term stability and achieved the highest total turnover number of any known palladium system.
Article
Chemistry, Physical
Ashlee K. Hauble, Michael Y. Toriyama, Stephan Bartling, Ali M. Abdel-Mageed, G. Jeffrey Snyder, Susan M. Kauzlarich
Summary: Low-dimensional materials, such as layered Zintl phases, have unique properties that make them desirable for various applications. The complex structure and composition of layered Zintl phases pose challenges in producing phase-pure bulk samples for characterization. Eu11Zn4Sn2As12, a layered Zintl phase of significant complexity, exhibits magnetic, electronic, and thermoelectric properties, making it a promising material for further optimization and exploitation in thermoelectric applications.
CHEMISTRY OF MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Yue Hu, Xinmin Li, Mingyang Liu, Stephan Bartling, Henrik Lund, Paul J. Dyson, Matthias Beller, Rajenahally V. Jagadeesh
Summary: Catalytic hydrodeoxygenation is a crucial technology for converting biomass-based feedstocks into essential chemicals and fuels. This study reports the preparation and application of Ni nanoparticles supported on ZSM-5 as an efficient hydrodeoxygenation catalyst. The Ni-based nanoparticles exhibit selective hydrodeoxygenation of various functional substrates, showcasing their versatility.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Engineering, Biomedical
Christian Polley, Thomas Distler, Caroline Scheufler, Rainer Detsch, Henrik Lund, Armin Springer, Dominik Schneidereit, Oliver Friedrich, Aldo R. Boccaccini, Hermann Seitz
Summary: Bone healing is a complex process that involves various factors such as mechanical, chemical, and electrical cues. Scientists worldwide aim to create synthetic biomaterials that combine these factors to achieve tailored and controlled tissue regeneration. This study presents a method using additive manufacturing techniques to create macroporous biomaterial scaffolds made of a piezoelectric and bioactive ceramic-crystallized glass composite. These scaffolds show suitable mechanical strength, bioactivity, and piezoelectric properties, making them promising candidates for bone tissue engineering.
MATERIALS TODAY BIO
(2023)
Article
Chemistry, Physical
Shuoping Ding, Jose Balena Gabriel Filho, Tim Peppel, Simon Haida, Jabor Rabeah, Norbert Steinfeldt, Jennifer Strunk
Summary: Two-dimensional ZnIn2S4 nanosheets were synthesized via a trisodium citrate-assisted hydrothermal method and used for the oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) and 5-formyl-2-furan (FFCA) with atmospheric O-2 under visible light irradiation. The conversion of HMF reached 95%, and the DFF selectivity was 70% after 1.5 h of illumination. Photogenerated holes (h(+)), O-2(-) and carbon-centred radicals are the dominant reaction species.
SUSTAINABLE ENERGY & FUELS
(2023)
Article
Chemistry, Physical
Shuoping Ding, Igor Medic, Norbert Steinfeldt, Tianao Dong, Tim Voelzer, Simon Haida, Jabor Rabeah, Juncheng Hu, Jennifer Strunk
Summary: Constructing hierarchical and ultrathin-structured metal sulfides is beneficial for efficient hydrogen evolution catalysts. In this study, ZnIn2S4 hollow nanoflowers composed of ultrathin nanosheets were creatively synthesized through a trisodium citrate-mediated and stirring-assisted solvothermal method. The optimized ZnIn2S4 hollow nanoflowers exhibited a high photocatalytic hydrogen generation rate and can be obtained without the need for a cocatalyst.
Article
Chemistry, Physical
Andrey S. Skrypnik, Henrik Lund, Qingxin Yang, Evgenii V. Kondratenko
Summary: A simple wetness impregnation of ferrous oxalate dihydrate with an alkali metal carbonate solution leads to active and selective catalysts for CO2 hydrogenation. The in situ formation of active iron carbide and Fe3O4 phases under reaction conditions eliminates the need for catalyst reduction. The kind of alkali metal and the amount of Rb mainly affect the rate of direct CO2 conversion to CH4, while CO hydrogenation to higher hydrocarbons is not significantly influenced.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Chenyang Wang, Luis Miguel Azofra, Phong Dam, Edelman J. Espinoza-Suarez, Hieu Trung Do, Jabor Rabeah, Angelika Brueckner, Osama El-Sepelgy
Summary: In this study, an intramolecular endo-selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols was reported. The reaction resulted in the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation. This method could be used for the selective (Z)-hydroxymethylation of o-hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggested a concerted beta-hydrogen elimination event to take place in the triplet state.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Prasenjit Das, Gouri Chakraborty, Jerome Roeser, Sarah Vogl, Jabor Rabeah, Arne Thomas
Summary: Multicomponent reactions (MCRs) are employed to incorporate different functionalities into stable covalent organic frameworks (COFs). In this study, irreversible three-component Doebner reaction is utilized to synthesize chemically stable DMCR-COFs equipped with acid-base bifunctionality. These DMCR-COFs exhibit superior photocatalytic H2O2 evolution compared to Imine-1, showcasing their potential as materials for solar to chemical energy conversion.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Ruiyang Qu, Shuxin Mao, Jana Weiss, Vita A. Kondratenko, Evgenii V. Kondratenko, Stephan Bartling, Haifeng Qi, Annette-Enrica Surkus, Kathrin Junge, Matthias Beller
Summary: The hydrogenation of amides, a challenging reaction usually performed at high temperatures, has been achieved under milder conditions using a new Pt-MoOx/TiO2 catalyst. This catalyst system enables the selective hydrogenation of various amides and imides.
CATALYSIS SCIENCE & TECHNOLOGY
(2024)