Article
Chemistry, Organic
Zheng-Hai Wang, Dong-Hui Wang
Summary: A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported, with moderate to good yields under mild reaction conditions. Large-scale syntheses of Ezutromid and Flunoxaprofe are demonstrated in one or two steps. The proposed catalytic mechanism involves Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation.
Article
Chemistry, Multidisciplinary
Yunhui Feng, Hang Luo, Fangnian Yu, Qian Liao, Luqing Lin
Summary: Here, we present a visible-light-promoted single nickel catalysis for achieving various C-N couplings of aryl chlorides/bromides and diverse N-nucleophiles using sodium iodide as the activator. The single nickel catalyst plays a dual role in halogen exchange and C-N coupling, which are crucial for obtaining the desired coupling products. This catalytic process eliminates the need for an exogenous photocatalyst and offers a sustainable and efficient approach for mild C-N coupling. Experimental studies, along with UV-vis and NMR analyses, demonstrate that the halogen exchange between both Ni-II and Ni-III-halide complexes and the iodide anion is a significant process in the formation of coupling products.
Article
Chemistry, Multidisciplinary
Jian Huang, Han-Han Kong, Si-Jia Li, Rui-Jin Zhang, Hao-Dong Qian, Dan-Ran Li, Jin-Yu He, Yi-Nuo Zheng, Hao Xu
Summary: The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts using chiral N,N,P-ligands has been successfully developed. This method demonstrates a broad substrate scope and wide functional group tolerance, producing propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The approach was further validated by late-stage functionalization of marketed pharmaceuticals.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Xin-Yang Lv, Roman Abrams, Ruben Martin
Summary: This article describes the development of a copper-catalyzed C(sp(3))-amination of proaromatic dihydroquinazolinones derived from ketones. The reaction utilizes open-shell species generated through homolytic C-C bond cleavage driven by aromatization. The protocol is characterized by its simplicity and generality, allowing for chemical diversification of advanced intermediates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jinghua An, Zhuyan Gao, Yehong Wang, Zhixin Zhang, Jian Zhang, Lu Li, Bo Tang, Feng Wang
Summary: An efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins has been developed without any additives, leading to the successful synthesis of various amines and transformation of nitrobenzene derivatives in high yields.
Article
Chemistry, Organic
Joseph P. Tassone, Travis Lundrigan, Trent D. Ashton, Mark Stradiotto
Summary: This study successfully synthesized potentially useful 4-amino-1,8-naphthalimides fluorescent probes using a new method, highlighting the significance of Ni-catalyzed reactions in this process.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Koji Hirano
Summary: The development of new C-N bond forming strategies is crucial due to the importance of nitrogen atom in bioactive molecules and functional materials. This account presents the nitrogen-umpolung-enabled copper-catalyzed highly selective amination protocols developed by the author's research group. The application of these methods to the synthesis of alkyl-amines with rich functionality is demonstrated.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2023)
Article
Chemistry, Organic
Yan-Ling Tang, Mei-Ling Li, Jin-Chun Gao, Yun Sun, Lu Qu, Feng Huang, Ze-Wei Mao
Summary: An efficient Cu(II)-vasicine catalytic system has been developed for intramolecular CAN bond formation, allowing for regioselective 2-amination of o-haloanilides with aqueous ammonia in EtOH. This strategy offers advantages such as good regioselectivity, high yields, and functional group tolerance.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Zhen-Sheng Jia, Qiang Yue, Ya Li, Xue-Tao Xu, Kun Zhang, Bing-Feng Shi
Summary: In this study, a copper-catalyzed mono-selective C-H amination of ferrocenes assisted by 8-aminoquinoline was successfully demonstrated, allowing for efficient installation of a range of amines to the ortho-position of ferrocene amides under mild conditions. The gram-scale reaction proceeded smoothly, and the directing group could be easily removed under basic conditions.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yuxue Zhang, Mengxue Pei, Fan Yang, Yangjie Wu
Summary: A highly efficient protocol for the synthesis of 4-aminated 1-naphthylamine derivatives using readily available azodicarboxylates and picolinamide as a bidentate directing group is reported. The reaction proceeds smoothly in acetone at room temperature without the need for a base or external oxidant, resulting in good to excellent yields.
Article
Chemistry, Organic
Jinpeng Li, Changyu Huang, Daheng Wen, Qingshu Zheng, Bo Tu, Tao Tu
Summary: A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been successfully achieved under mild conditions. The protocol offers a broad substrate scope with excellent functional group tolerance at a low catalyst loading, making it powerful for synthesizing various aromatic amines. Selective coupling of aryl chlorides to the amino fragments of amides rather than the carbonyl moieties expands the usage of inactive amides.
Article
Chemistry, Organic
Weiqiao Lan, Jiatong Zhu, Buweihailiqiemu Abulaiti, Genyuan Chen, Zhihao Zhang, Nan Yan, Jie-Ping Wan, Xiaomei Zhang, Lihua Liao
Summary: An efficient zinc-catalyzed amination reaction has been developed for the para-selective amination of free anilines and free phenols with quinoneimides, leading to C-N bond formation via a 1,6-addition pathway. This protocol not only offers a promising approach for constructing structurally diverse p-phenylenediamine compounds with excellent yields, but also extends the application of the quinoneimide-involved 1,6-addition reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaobin Tan, Wenfang Xiong, Baiyao Zhu, Hongjian Liu, Wanqing Wu, Huanfeng Jiang
Summary: A novel methodology for the primary amination of aromatic C(sp2)-H bond using hydroxylamine derivative as ammonia surrogates has been developed. Various aromatic primary amines were synthesized with a cost-effective and convenient copper oxide catalyst without external oxidant, exhibiting good functional group tolerance, wide substrate scope, easy availability of substrates, and a simple work-up procedure. This method also allows for the late-stage modification of drug-like small molecules with complex structures.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Analytical
Shivam Kumar Gautam, Siddhartha Panda
Summary: A highly sensitive copper-based nanocomposite for NH3 detection was reported in this study. The copper-ethylenediamine (Cu-en) nanocomposite functionalized over PANI was utilized for gas sensing, and it detected NH3 concentrations as low as 2 ppm. The sensing mechanism was studied by in-situ IV characteristics and impedance spectroscopy, and it was found that Cu2+ had a strong affinity for NH3, enhancing the sensor response to 100 ppm NH3.
Article
Chemistry, Multidisciplinary
Harshita Shet, Manisha Patel, Jyoti M. Waikar, Pavan M. More, Yogesh S. Sanghvi, Anant R. Kapdi
Summary: In this study, a highly efficient room-temperature dimethylamination of chloroheteroarenes was achieved by in-situ generation of dimethylamine using N,N-dimethylformamide (DMF) as a precursor. The reaction exhibited a broad substrate scope, including various heteroarenes and commercially relevant drugs.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Xinyi Chen, Junfeng Chen, Nawal M. Alghoraibi, Danielle A. Henckel, Ruixian Zhang, Uzoma O. Nwabara, Kenneth E. Madsen, Paul J. A. Kenis, Steven C. Zimmerman, Andrew A. Gewirth
Summary: A Cu-polyamine hybrid catalyst was developed to significantly enhance the selectivity for ethylene production in CO2 electrochemical conversion. Incorporating polyamine altered surface reactivity, leading to improved product selectivity at high current densities.
Article
Multidisciplinary Sciences
Shaohong Peng, Pei Guo, Xiao Lin, Ying An, Kong Hung Sze, Matthew Ho Yan Lau, Zhefan Stephen Chen, Qianwen Wang, Wen Li, Jacquelyne Ka-Li Sun, Sum Yi Ma, Ting-Fung Chan, Kwok-Fai Lau, Jacky Chi Ki Ngo, Kin Ming Kwan, Chun-Ho Wong, Sik Lok Lam, Steven C. Zimmerman, Tiziano Tuccinardi, Zhong Zuo, Ho Yu Au-Yeung, Hei-Man Chow, Ho Yin Edwin Chan
Summary: The research demonstrates that CAG repeat RNA-induced NUDT16 deficiency is a pathogenic mechanism of polyQ diseases, and it holds potential therapeutic implications for treating HD and other polyQ diseases.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Medicinal
Ke Li, Sarah B. Krueger, Steven C. Zimmerman
Summary: DM1 is a neuromuscular disorder caused by repeat expansion in the DMPK gene. A rationally designed small molecule has been found to selectively inhibit transcription and improve molecular features in DM1 model cells. This compound represents a new structure type for potential future optimization.
Article
Chemistry, Multidisciplinary
Thao M. Xiong, Edzna S. Garcia, Junfeng Chen, Lingyang Zhu, Ariale J. Alzona, Steven C. Zimmerman
Summary: The research presents a modular approach utilizing noncovalently cross-linked single chain nanoparticles (SCNP) to selectively bind catalyst cofactors and substrates, resulting in increased catalytic activity in Cu-catalyzed alkyne-azide cycloaddition reaction and Ru-catalyzed cleavage of allylcarbamate groups compared to free catalysts.
CHEMICAL COMMUNICATIONS
(2022)
Article
Polymer Science
Dhawal R. Thakare, Thao M. Xiong, Ian L. Flueck, Ephraim G. Morado, Steven C. Zimmerman, Nancy R. Sottos
Summary: This work reports pH-responsive microcapsules with triggered release over a wide range of acidic pH values, which are robust enough to be incorporated in commercial solvent-based epoxy coatings. The degradation and release kinetics of the microcapsules are quantified at various pH levels. Inhibition efficiencies up to 70% are achieved in acidic saltwater solutions.
MACROMOLECULAR CHEMISTRY AND PHYSICS
(2022)
Article
Multidisciplinary Sciences
Bryce R. Van Dam, Mary A. Zeller, Christian Lopes, Ashley R. Smyth, Michael E. Boettcher, Christopher L. Osburn, Tristan Zimmerman, Daniel Proefrock, James W. Fourqurean, Helmuth Thomas
Summary: Long-term Blue Carbon burial in seagrass meadows is influenced by other carbon and alkalinity exchanges, with ecosystem calcification-induced CO2 emissions being the main contributor. Overestimation of net carbon sequestration potential may occur if these emissions are not taken into account.
Editorial Material
Environmental Sciences
Bryce Van Dam, Christian Lopes, Mary A. Zeller, Mariana Ribas-Ribas, Hongjie Wang, Helmuth Thomas
FRONTIERS IN MARINE SCIENCE
(2021)
Article
Environmental Sciences
Catia Milene Ehlert von Ahn, Jan C. Scholten, Christoph Malik, Peter Feldens, Bo Liu, Olaf Dellwig, Anna-Kathrina Jenner, Svenja Papenmeier, Iris Schmiedinger, Mary A. Zeller, Michael Ernst Boettcher
Summary: This study characterizes and evaluates the hydrogeochemical gradients in the mixing zone of the Wismar Bay in the southern Baltic Sea, Germany, revealing that different fresh water sources, including SGD, contribute to the water balance of the bay. Enhanced concentrations of radium isotopes and other dissolved substances in surface waters indicate benthic-pelagic coupling and anthropogenic impacts on sediment layers.
FRONTIERS IN ENVIRONMENTAL SCIENCE
(2021)
Article
Biochemistry & Molecular Biology
JuYeon Lee, Ke Li, Steven C. Zimmerman
Summary: A selective DNA-modifying small molecule has been developed that targets disease-specific structures and mismatches involved in myotonic dystrophy type 1 (DM1). This molecule has shown to inhibit the synthesis of toxic transcripts and improve disease features in DM1 model cells. The strategy used may be applicable for the treatment of other repeat expansion diseases.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Nicholas F. Garza, Solaire A. Finkenstaedt-Quinn, Ginger Shultz, Steven C. Zimmerman
Summary: Organic chemistry courses attract students from diverse majors and interests, but it is challenging to personally appeal to students in high enrollment courses. By implementing a writing assignment that prompts students to choose an organic compound and write about a personal connection, students were able to identify the relevance of organic chemistry to their lives.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Article
Biochemistry & Molecular Biology
Sarah B. Krueger, Amie N. Lanzendorf, Hyoeun Heather Jeon, Steven C. Zimmerman
Summary: This study reports a method of assembling therapeutic agents in situ via aldehyde-amine condensation to target DNA and RNA sequences. Small molecule targeting agents were synthesized and screened against the target nucleic acid sequence, and the assembly of fragments was confirmed in the presence of DM1-relevant nucleic acid sequences. The resulting hit combinations of aldehyde and amine inhibited the formation of r(CUG)(exp) at low micromolar levels and corrected mis-splicing defects in DM1 model cells.
Article
Chemistry, Multidisciplinary
Ephraim G. Morado, Mara L. Paterson, Douglas G. Ivanoff, Hsuan-Chin Wang, Alayna Johnson, Darius Daniels, Aoon Rizvi, Nancy R. Sottos, Steven C. Zimmerman
Summary: A mechanism for degrading polymers called cyclization-triggered chain cleavage (CATCH cleavage) that achieves dual requirements of strength and degradability has been reported. CATCH cleavage features a glycerol-based acyclic acetal unit as a trap for controlled chain breaks. Organic acid induces transient chain breaks with subsequent cyclization to fully depolymerize the polymer backbone at room temperature. This strategy has the potential for upcycling and may be applicable to various synthetic polymers and their waste streams.
Article
Chemistry, Medicinal
Sarah B. Krueger, Steven C. Zimmerman
Summary: This study reports a target-guided screening method based on dynamic covalent chemistry for identifying multitarget inhibitors. A library of amine- or aldehyde-containing fragments was synthesized and assembled, resulting in a diverse set of hit combinations. These hit combinations selectively and cooperatively inhibited transcription of myotonic dystrophy type 1 and Huntington's disease repeat sequences in vitro.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Ecology
Bryce Van Dam, Nele Lehmann, Mary A. Zeller, Andreas Neumann, Daniel Proefrock, Marko Lipka, Helmuth Thomas, Michael Ernst Boettcher
Summary: This study quantified the net sediment-water exchange of alkalinity using multiple methods and found that the sediment-water irrigation rates in the southern North Sea were higher than previously estimated. The net alkalinity fluxes in the Baltic Sea were relatively low, while carbonate mineral dissolution, precipitation, and sulfide re-oxidation appeared to play important roles in shaping net sediment-water fluxes in the North Sea and Baltic Sea.
Article
Polymer Science
Edzna S. Garcia, Thao M. Xiong, Abygail Lifschitz, Steven C. Zimmerman
Summary: A Ru-containing single chain nanoparticle was prepared using radical polymerization, post-polymerization functionalization, and coordination of Ru. The catalytic SCNP showed higher catalytic activity for Ru-catalyzed cleavage of allylcarbamates compared to the free catalyst, with a higher percent conversion and initial rate of reaction observed in buffer and cell media. The SCNP also demonstrated tandem catalysis with beta-galactosidase.
