Article
Chemistry, Organic
Alafate Adili, Aniket V. V. Sole, Bishwaprava Das, Megan E. Matter, Daniel Seidel
Summary: In the presence of a thiourea-carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet-Spengler reactions with a range of aldehydes. The reaction exhibits good compatibility with aromatic aldehydes, accepting diverse substituents at various positions on the ring. Electron-deficient tryptamines can also be used as substrates. Furthermore, the fluorenyl protecting group can be easily removed without affecting the enantioselectivity of the product.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Kanji Niwa, Masao Ohashi, Kaili Xie, Chen-Yu Chiang, Cooper S. Jamieson, Michio Sato, Kenji Watanabe, Fang Liu, K. N. Houk, Yi Tang
Summary: We have discovered biosynthetic pathways that can produce and transform conjugated octaenes and nonaenes into complex natural products. The biosynthesis of (-)-PF1018 involves an enzyme called PfB, which controls the regio-, stereo-, and periselectivity of multiple reactions starting from a conjugated octaene. By using PfB as a starting point, we found a homologous enzyme, BruB, that facilitates diene isomerization, tandem 8π-6π-electrocyclization, and a 1,2-divinylcyclobutane Cope rearrangement to generate a novel compound not previously found in nature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Crystallography
Weiqing She, Zhenzhen Xu, Lianjie Zhai, Junlin Zhang, Jie Huang, Weiqiang Pang, Bozhou Wang
Summary: Due to the introduction of oxygen atoms, N-oxide energetic compounds possess unique advantages in terms of oxygen balance, detonation properties, and energy density, which have attracted extensive attention from researchers worldwide. This article provides a comprehensive review of the synthetic strategies for two categories of N-oxides, azine N-oxides and azole N-oxides, and discusses the reaction mechanisms of aromatic N-oxide frameworks and their applications in creating high-energy substances. Furthermore, the energetic properties of N-oxide energetic compounds are compared and summarized.
Review
Acoustics
Ingrid V. Machado, Jhonathan R. N. dos Santos, Marcelo A. P. Januario, Arlene G. Correa
Summary: By utilizing ultrasound-assisted multicomponent reactions under heterogeneous catalysis, it is possible to efficiently synthesize biologically active organic compounds with reduced costs and energy consumption.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Gemma A. Di Iulio, Mary F. Mahon, Lorenzo Caggiano
Summary: Pancratistatin framework can be accessed through a concise synthetic route without the need for metal catalysis or activated substrates. This method offers the possibility of generating various pancratistatin analogues for further development.
Article
Chemistry, Multidisciplinary
Liam A. McLean, Matthew W. Ashford, James W. B. Fyfe, Alexandra M. Z. Slawin, Andrew G. Leach, Allan J. B. Watson
Summary: We have reported a method for synthesizing chiral vicinal chloroamines through asymmetric protonation using chiral Bronsted acids. The process is highly selective and the origins of asymmetry and the effects of catalyst substitutions have been clarified by DFT calculations. Additionally, we have demonstrated the utility of this method in synthesizing a wide range of heterocycle-substituted aziridines and vicinal diamines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Stanislav V. Shcherbakov, Alexander V. Aksenov, Maksim V. Vendin, Viktoria Yu. Shcherbakova, Anna Yu. Ivanova, Maksim O. Shcheglov, Sergei N. Ovcharov, Michael Rubin
Summary: Unusual rearrangements were observed during Bronsted acid-assisted peri-annulations of 1H-perimidines with 5-alkynylpyrimidines. The reactions take different pathways depending on the nature of the acetylene precursor, ultimately leading to the formation of 7-formyl-1,3-diazopyrenes.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Christina Jaeger, Mona Haase, Katja Koschorreck, Vlada B. Urlacher, Jan Deska
Summary: Biocatalytic oxidation of acylated hydroxylamines enables selective introduction of nitrogen functionalities by activating allylic C-H bonds. Utilizing laccases or oxidase/peroxidase couple with air as the oxidant, acylnitroso species are generated under mild aqueous conditions. These reactive intermediates undergo C-N bond formation through an ene-type mechanism, providing high yields in both intramolecular and intermolecular enzymatic aminations. Investigations on different pathways and labelling studies provide insight into the promiscuity of oxidoreductases as catalysts for nitroso-based transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jennifer Smith, Aysecik Kacmaz, Chao Wang, Barbara Villa-Marcos, Jianliang Xiao
Summary: A series of chiral cyclometalated iridium complexes were synthesized and studied for asymmetric transfer hydrogenation reactions using formic acid as the hydrogen source, showing different activities and enantioselectivities, with the most effective ones achieving up to 63% ee in asymmetric reductive amination of ketones and 77% ee in reduction of pyridinium ions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Yuk Ping Chin, Nicholas W. See, Ian D. Jenkins, Elizabeth H. Krenske
Summary: This review analyzes the advances and trends in the computational elucidation of organic reaction mechanisms over the past 10-15 years, focusing on newly possible mechanistic problem types and summarizing the methodological developments that have enabled these advancements. Case studies from three representative areas of organic chemistry illustrate common themes such as modeling increasingly complex systems, recognizing the mechanistic roles of non-covalent interactions, and exploring dynamical features of reaction mechanisms, while also identifying new challenges in the field.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Martin-Louis Y. Riu, Wesley J. Transue, Jan M. Rall, Christopher C. Cummins
Summary: A novel diazene compound was synthesized in this study, which underwent a series of reactions to form corresponding cycloadducts. Structural data of the cycloadducts were obtained, and the thermolysis process of this compound along with its kinetic parameters were investigated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Patrick Q. Kelly, Alexander S. Filatov, Mark D. Levin
Summary: This study presents a synthetic cycle and detailed mechanistic studies, demonstrating the potential of terminal transition metal nitrides as valuable single-atom transfer reagents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiaming Zou, Lei Xu, Yurong Tang, Wentao Wang, Yunfei Cai
Summary: The asymmetric synthesis of bridged tetrahydrobenzo[b]azepine and oxepine derivatives has been achieved through chiral Bri nsted acid catalyzed asymmetric aza-Piancatelli rearrangement/Michael addition sequence. The reaction proceeds under mild reaction conditions to afford the final bridged cyclic products in good yields with excellent enantio- and diastereoselectivities.
Article
Chemistry, Organic
Wen Hu, Jiaqi Xiang, Qi Zhou, Xinyu Gao
Summary: This study found that readily available protonated 2,2'-bipyridinium salts can be used as Bronsted acid catalysts to accelerate various organic transformations with good to excellent yields. These transformations include the hydration of aromatic alkynes, etherification of alcohols, cyclotrimerization of aliphatic aldehydes, Ritter reaction, Mannich reaction, Biginelli reaction, preparation of substituted alkenes from alcohols, synthesis of spirooxindole, bisindolylmethane, and noncyclized tetraketone. The results suggest enormous potentiality in the development of the protonated 2,2' bipyridinium catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zheng-Jia Shen, Chen Zhu, Xiao Zhang, Chao Yang, Magnus Rueping, Lin Guo, Wujiong Xia
Summary: This article describes a selective (deutero)hydrodefluorination reaction via electrolysis, which achieves remarkable chemoselectivity control by the addition of different organoboron sources. The method is operationally simple, scalable, and provides access to high-value building blocks for medicinal chemistry in one step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Jose J. Delgado-Marin, Alejandra Rendon-Patino, Vijay Kumar Velisoju, Gadde Sathish Kumar, Naydu Zambrano, Magnus Rueping, Jorge Gascon, Pedro Castano, Javier Narciso, Enrique V. Ramos-Fernandez
Summary: We demonstrate that ZIFs used as catalysts for CO2 insertion suffer from irreversible degradation by leaching, leading to decreased stability and catalytic activity. Additional treatments are necessary to improve their stability.
CHEMISTRY OF MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Jean Michel Merkes, Gerhard Raabe, Fabian Kiessling, Magnus Rueping, Srinivas Banala
Summary: The isolation and characterization of a kinetically stable oxadiazaborinine (ODB) dye are described in this study. It undergoes an unexpected thermal boron rearrangement, which results in a color change and increased fluorescence. This controllable reaction allows for the practical use as a time-temperature indicator probe, offering advantages such as photostability, non-reversibility, and environmental friendliness.
ADVANCED OPTICAL MATERIALS
(2023)
Editorial Material
Multidisciplinary Sciences
Huifeng Yue, Chen Zhu, Magnus Rueping
Article
Nanoscience & Nanotechnology
David Ohayon, Dominik Renn, Shofarul Wustoni, Keying Guo, Victor Druet, Adel Hama, Xingxing Chen, Iuliana Petruta Maria, Saumya Singh, Sophie Griggs, Bob C. Schroeder, Magnus Rueping, Iain McCulloch, Sahika Inal
Summary: We developed an electrochemical transistor with an n-type conjugated polymer film for sensitive and selective glucose detection in bodily fluids. By studying the impact of the polymer chemical structure on film surface properties and enzyme adsorption behavior, we found that a negatively charged, smooth, and hydrophilic film surface provides the best environment for enzyme adsorption and maximizes sensor performance.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Saidkhodzha Nematulloev, Arunachalam Sagadevan, Badriah Alamer, Aleksander Shkurenko, Renwu Huang, Jun Yin, Chunwei Dong, Peng Yuan, Khursand E. Yorov, Azimet A. Karluk, Wasim J. Mir, Bashir E. Hasanov, Mohamed Nejib Hedhili, Naveen M. Halappa, Mohamed Eddaoudi, Omar F. Mohammed, Magnus Rueping, Osman M. Bakr
Summary: This study reports the synthesis of atomically precise copper hydride nanoclusters with a controlled defect, which were demonstrated to be highly selective catalysts for C-C cross-couplings. The work highlights the potential of defective nanoclusters as model systems for investigating individual defects, correlating defects with physicochemical properties, and rationally designing new nanoparticle catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Haifeng Chen, Chen Zhu, Huifeng Yue, Magnus Rueping
Summary: In this study, a nickel-catalyzed, three-component reductive protocol for group 14 element hetero-difunctionalization of 1,3-enynes using electrochemistry is described. The method is mild, selective, and general, allowing for the silyl-, germanyl-, and stannyl-alkylation of enynes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Serik Zhumagazy, Chen Zhu, Huifeng Yue, Magnus Rueping
Summary: This article describes a nickel-catalyzed C-Se cross-coupling reaction between aryl iodides and selenols. The newly developed catalytic methodology provides easy access to various asymmetric selenium-containing compounds. The reaction exhibits excellent functional group tolerance, a wide range of substrates, high efficiency, and operates under mild conditions. Importantly, the protocol can be readily scaled up to gram-scale reactions without a loss of yield.
Article
Multidisciplinary Sciences
Liuzhuang Xing, Qian Yang, Chen Zhu, Yilian Bai, Yurong Tang, Magnus Rueping, Yunfei Cai
Summary: In this study, the authors successfully incorporated privileged homogeneous bipyridyl-based Ni-catalysts into highly ordered and crystalline potassium poly(heptazine imide) (K-PHI), achieving the development goal of heterogeneous metallaphotocatalysis. The LnNi-PHI catalysts exhibit superior chemical stability and recyclability in C-P, C-S, C-O and C-N cross-coupling reactions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Gadde Sathish Kumar, Chen Zhu, Rajesh Kancherla, Prashant S. S. Shinde, Magnus Rueping
Summary: An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. Valuable phenethylamines are synthesized at room temperature in good yields. The reaction is distinct from conventional and photochemical couplings, and the role of Ni(II) organometallic complexes and electrodes in the reaction mechanism are examined.
Review
Chemistry, Physical
Sam Mathew, Dominik Renn, Magnus Rueping
Summary: Amine transaminases play a crucial role in the synthesis of chiral amines, which are essential building blocks in pharmaceuticals and fine chemicals. Advances in enzyme discovery, process engineering, and protein engineering have significantly enhanced the use of transaminases in organic synthesis. Enzymatic cascade engineering has emerged as an efficient and environmentally friendly approach for chiral amine synthesis, allowing the generation of valuable products from inexpensive starting materials. This review focuses on the utilization of amine transaminases in enzymatic and chemoenzymatic cascades for chiral amine synthesis.
Article
Chemistry, Physical
Haifeng Chen, Chen Zhu, Huifeng Yue, Magnus Rueping
Summary: An efficient cobalt-catalyzed carbon-germanium bond formation method has been developed, providing access to a wide range of functionalized germane-containing compounds. This method shows a broad scope and good tolerance toward various functional groups, and is conducted under mild reaction conditions. Mechanistic studies shed light on the unexpected reaction pathway and sequential activation of different electrophiles.
Article
Biotechnology & Applied Microbiology
Ram Karan, Dominik Renn, Shuho Nozue, Lingyun Zhao, Satoshi Habuchi, Thorsten Allers, Magnus Rueping
Summary: This study presents a genetic engineering and chemical modification approach to functionalize the major gas vesicle nanoparticle (GVNP) protein, GvpA. By introducing combinatorial cysteine mutagenesis within GvpA and expanding the N- and C-terminal regions, GvpA single, double, and triple cysteine variant libraries were generated. Thiol-maleimide chemistry was used to introduce biotechnologically relevant activities to the GVNPs. This approach significantly expands the bioengineering and functionalization potential of these novel protein nanomaterials.
JOURNAL OF NANOBIOTECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Wenhuan Huang, Chenyang Su, Chen Zhu, Tingting Bo, Shouwei Zuo, Wei Zhou, Yuanfu Ren, Yanan Zhang, Jing Zhang, Magnus Rueping, Huabin Zhang
Summary: The solar-driven evolution of hydrogen from water using particulate photocatalysts is a promising method for achieving a stable supply of renewable energy. However, the efficiency of photocatalytic water splitting is low due to sluggish electron-hole pair separation kinetics. In this study, highly oxidized Mo species incorporated into Cd0.5Zn0.5S nanorods exhibit significantly enhanced photocatalytic efficiency through inhibited electron-hole recombination.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chunwei Dong, Ren-Wu Huang, Arunachalam Sagadevan, Peng Yuan, Luis Gutierrez-Arzaluz, Atanu Ghosh, Saidkhodzha Nematulloev, Badriah Alamer, Omar F. Mohammed, Irshad Hussain, Magnus Rueping, Osman M. Bakr
Summary: In this study, a synthesis method for obtaining an atomically precise nanoparticle with a surface-defective analogue is reported. The loss of a single surface atom drastically alters the reactivity of the nanoparticle, showing promising activity for click chemistry, especially photoinduced azide-alkyne cycloaddition. This study not only uncovers the effect of single-surface atom modification on nanoparticle properties but also demonstrates the potential of single-atom surface modification as a means for designing nanoparticle catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
