Article
Chemistry, Organic
Bang-Hong Zhang, Wen Bao, Fu Cheng, Ke-Yang Yu, Jia-Xuan Wang, Zi-Hao Zhang, Long-Jun Dong, Ze-Sen Xue, Dao-Yong Zhu, Xue-Tao Xu, Shao-Hua Wang
Summary: A Rh(I)-catalyzed [5 + 2]/[2 + 2] cycloaddition cascade has been developed to efficiently form a complex and highly strained [4-5-6-7] tetracyclic framework with good yields and excellent diastereoselectivities. The formation of three rings, three C-C bonds, and four contiguous stereocenters is achieved through the readily construction of rare sterically congested multi-substituted cyclobutanes using Michael addition and a Mannich reaction cascade.
Article
Chemistry, Organic
Bang-Hong Zhang, Wen Bao, Fu Cheng, Ke-Yang Yu, Jia-Xuan Wang, Zi-Hao Zhang, Long-Jun Dong, Ze-Sen Xue, Dao-Yong Zhu, Xue-Tao Xu, Shao-Hua Wang
Summary: A Rh(I)-catalyzed [5 + 2]/[2 + 2] cycloaddition cascade was developed to synthesize a complex and highly strained [4-5-6-7] tetracyclic framework with high yield and diastereoselectivity. Three rings, three C-C bonds, and four contiguous stereocenters were efficiently formed during the transformation. Mechanistically, the sterically congested multi-substituted cyclobutanes were readily constructed through a Michael addition and Mannich reaction cascade.
Article
Chemistry, Organic
Yong-Cheng Yang, Te-Ri-Gen Bao, Shu-Yi Zhu, Lu-Qi Liu, Guo-Qing Long, Zi-Feng Guo, Xuan-Li Liu, Xiao-Xu Gao, Jing-Ming Jia, An-Hua Wang
Summary: Chinorlactone A (1), along with two SNTs schisdilactones V and W (2 and 3), were isolated from Schisandra chinensis. Extensive spectroscopic analyses and single-crystal X-ray diffraction confirmed their structures and absolute configurations. A hypothetical biosynthetic pathway for 1 was proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Min Gao, Yanshu Luo, Qianlan Xu, Yukun Zhao, Xiangnan Gong, Yuanzhi Xia, Lin Hu
Summary: The research achieved a unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides using a chiral phase-transfer catalyst (PTC). This method provides a distinct way to access valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. The DFT calculations were performed to rationalize the high enantioselectivity observed in the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Chenikkayala Siva Sankara, Irishi N. N. Namboothiri
Summary: The Hauser-Kraus annulation allows for the synthesis of nitrogen-containing aromatic heterocycles through a cascade of reactions, resulting in high selectivity and yield.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: The study successfully achieved multi-functionalization of the pyridine motif in indolizine through [5+1] annulative construction, introducing three different functional groups at the C5, C6, and C7 positions. The solvent (2-MeTHF) and the hydroxyl of 2-hydroxyacetophenones were found to play crucial roles in the successful cyclization event. Furthermore, the elaboration of the resulting scaffold and the potential expansion using other methyl ketones were also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Sambasivarao Kotha, Usha Nandan Chaurasia, Kunkumita Jena
Summary: Here, a simple synthetic approach for the synthesis of fused carbocyclic frameworks [5/6/5] and [5/5/5] from bis-adducts of norbornadiene and cyclohexadiene derivatives with 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene has been developed. The key step in this approach is atom-economic ring-rearrangement metathesis, and these ring systems are crucial in natural products. Highly congested polycyclic frameworks have been designed, incorporating molecular complexity in a minimal number of steps. These targets have up to seven stereo centers, making this strategy valuable in medicinal chemistry for designing diverse drug-like molecules.
Article
Chemistry, Multidisciplinary
Loic Habert, Kevin Cariou
Summary: In this study, the aerobic iodoarene catalysis was achieved by using a pyrylium photocatalyst under blue light irradiation, allowing for the use of low catalytic loading of both catalysts under very mild operating conditions. This unprecedented dual organocatalytic system provides a powerful and efficient methodology for spiro-cyclization of amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jiupeng Liu, Shuo Tang, Mengyao Zhao, Jianing Huai, Jingya Yu, Jingjing Zhao, Pan Li
Summary: The reactivity of vinyl epoxides/oxetanes/cyclopropanes towards arynes can lead to the synthesis of various functionalized phenanthrenes under mild conditions. This transition-metal-free cascade process involves a series of Diels-Alder reaction, ring-opening aromatization, and ene reaction. Vinyl epoxides/oxiranes show a preference for Diels-Alder reaction with arynes over nucleophilic attack.
Article
Chemistry, Multidisciplinary
Marie Auvray, Matthieu Jeanty, Philippe Jubault, Thomas Poisson
Summary: We developed a photoinduced Minisci reaction on a variety of diazines with high yields (28 examples, 44% to 89%). The reaction, using 4CzIPN (1 mol %) as a photoinitiator, was conducted under white LED irradiation and required a slightly excess of acid reagent (1.2 equiv.). Cyclization reactions were further explored to obtain novel N-heterocycles as building blocks for drug discovery programs. An extension of the reaction in continuous flow was also demonstrated. The mechanism of the transformation was studied and a plausible radical chain mechanism was proposed.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Mingyue Cui, Juan Li, Rongqiang Tian, Zheng Duan
Summary: A straightforward synthetic method was developed using tandem [5 + 1] carbonyl cyclization/[8 + 2] cycloaddition reactions of tropones and phosphiranes to synthesize structurally complex 6,5,7-fused tricyclic scaffolds. This one-pot reaction showed excellent regio- and periselectivity, with exclusive formation of the P-O bond and high-order [8 + 2] cycloaddition enabled by the highly reactive C=P bond.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Issei Nakamura, Masahiro Anada, Shunsuke Sueki, Kosho Makino, Keiji Mori
Summary: We have developed a sequential hydride shift process involving a [1,8]-hydride shift, leading to the synthesis of nine-membered carbocycle-fused piperidine derivatives in good yields. The use of 30 mol% Yb(OTf)(3) and 10 mol% iPr(2)NEt as catalysts is crucial for the success of this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Liwei Zhou, Xiaodong Liu, Haiyan Lu, Guobo Deng, Yun Liang, Yuan Yang, Jin-Heng Li
Summary: The study presents a novel method based on radical Smiles rearrangement strategy, utilizing cheap copper catalyst to achieve an unprecedented [3 + 2]/[3 + 2] carboannulation of dienynes with arylsulfonyl chlorides, resulting in cyclopenta[a]indene-fused quinolinones with excellent diastereoselectivity. This cascade method represents a new cycloaddition mode for dienyne chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yuanyuan Li, Longhui Duan, Biqiong Hong, Zhenhua Gu
Summary: This study developed a copper-catalyzed enantioselective ring-opening reaction, which can selectively advance the synthesis of different functionalized compounds starting from 2,2'-dibromo-6,6'-diiodo-1,1'-biphenyl. Through a series of functionalization reactions, a new and convenient approach for synthesizing functionalized axially chiral biphenyls was introduced.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada
Summary: This study describes the Pd-catalyzed stereoselective synthesis of decalins with one-carbon units bearing heteroatoms at the ring junction. The Pd-catalyzed cyclization of silyl enol ether resulted in the exclusive formation of the cis isomer (89%, >100/1 cis/trans). Conversely, Pd-catalyzed carboiodination and carboborylation reactions (with oxidative workup) provided products with yields of 56% (1/>100 cis/trans) and 69% (1/11 cis/trans), respectively.
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.