Article
Chemistry, Applied
Chuan Liu, Guangpeng Yan, Zonglang Wu, Youzhe Yang, Lin Yang, Jun Wang, Zibei Wan, Jun Wei, Ji Lu, Siping Wei, Dong Yi
Summary: This study reports an oxidant-free photocatalytic reaction that enables the cyclization of 2-cyanoaryl acrylamides with 2-bromocarbonyls, leading to the assembly of biologically important N-heterocycle-fused quinolinones. This reaction proceeds through a radical relay pathway, involving alkene difunctionalization and site-specific functionalization of inert C(sp(3))-H bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Multidisciplinary Sciences
Chi Zhang, Zhong-Liang Li, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: In recent years, there has been a renaissance in the enantioselective functionalization of common C(sp(3))-H bonds through a radical pathway. The authors summarize the main achievements in the field, identifying two main reaction pathways determining the stereochemistry, and provide an outlook on future challenges and opportunities.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Pan Peng, Yifan Zhong, Cong Zhou, Yongsheng Tao, Dandan Li, Qingquan Lu
Summary: We report an unprecedented copper/chromium catalytic system that converts inert alkyl C-H bonds into nucleophilic alkyl-Cr(III) species at room temperature, enabling carbonyl addition reactions with strong alkyl C-H bonds. Various aryl alkyl alcohols are obtained under mild reaction conditions, even on a gram scale. Furthermore, this new radical-to-polar crossover approach is applied to the 1,1-difunctionalization of aldehydes with alkanes and different nucleophiles. Mechanistic investigations reveal that the aldehyde not only acts as a reactant but also serves as a photosensitizer to recycle the copper and chromium catalysts.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Organic
Qiang Chen, Jingwen You, Tian Tian, Zhenyao Li, Myuto Kashihara, Hiroki Mori, Yasushi Nishihara
Summary: This paper describes the nickel-catalyzed reductive alkylation of aroyl fluorides with alkyl bromides, allowing the direct construction of C(sp2)-C(sp3) bonds and enabling the reaction between aroyl fluorides and alkyl bromides to form alkylarenes.
Article
Chemistry, Multidisciplinary
Srikrishna Bera, Runze Mao, Xile Hu
Summary: The enantioselective cross-coupling of non-activated alkyl halides with alkenyl boronates enables the synthesis of chiral alkyl boronates, which is a useful method for drug development. This reaction proceeds via nickel hydride insertion into an internal alkene followed by nickel-catalysed alkyl-alkyl cross-coupling.
Article
Chemistry, Multidisciplinary
Xiaoli Jiang, Feng-Tao Sheng, Yao Zhang, Gao Deng, Shaolin Zhu
Summary: Designing ligands in transition-metal catalyzed reactions is challenging. In this study, researchers applied the concept of combining multiple ligands to enhance catalytic efficiency and selectivity. As a result, they successfully achieved asymmetric remote hydroacylation and migratory acylation reactions to synthesize chiral α-aryl ketones.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Lili Feng, Xiaofan Chen, Ning Guo, Yuqiao Zhou, Lili Lin, Weidi Cao, Xiaoming Feng
Summary: A catalytic asymmetric a-C(sp(3))-H functionalization of alkyl silanes with benzosultams was achieved by combining photoredox and chiral Lewis acid catalysis. The success relied on the selection of a photocatalyst with appropriate redox potential and a non-nucleophilic solvent, leading to the synthesis of chiral organosilanes with two adjacent tri- and tetra-substituted stereocenters in high diastereo- and enantioselectivity (up to 99% ee, 94 : 6 dr) under mild reaction conditions.
Article
Multidisciplinary Sciences
Rui Wang, Cheng-Yu Wang, Peng Liu, Kang-Jie Bian, Chi Yang, Bing-Bing Wu, Xi-Sheng Wang
Summary: By using readily available aldehydes as alkyl radical precursors, we have developed an asymmetric radical decarbonylative azidation and cyanation reaction. This strategy exhibits a broad scope and excellent regioselectivity and enantioselectivity in asymmetric radical transformations.
Article
Chemistry, Multidisciplinary
Peng Xiong, Marcel Hemming, Sergei I. Ivlev, Eric Meggers
Summary: Merging electrochemistry with asymmetric catalysis offers a environmentally friendly and efficient strategy for synthesizing nonracemic chiral molecules. This study presents a catalytic asymmetric indirect electrolysis that achieves enantioselective nucleophilic alpha-C(sp(3))-H alkenylation of ketones by employing a combination of a redox mediator and a chiral-at-rhodium Lewis acid. The reaction demonstrates high yields and exceptional enantioselectivities without the need for additional oxidants.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Xiaowei Li, Yuxiu Li, Zhong Zhang, Xiaolin Shi, Ruihua Liu, Zemin Wang, Xiangqian Li, Dayong Shi
Summary: This nickel-catalyzed method enables the cross-coupling of allylic alkyl ethers with organoboron compounds, resulting in high yields, wide functional group tolerance, and good regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds demonstrate the practicality of this synthetic method.
Article
Chemistry, Organic
Pramod Rai, Satyadeep Waiba, Kakoli Maji, Dibyaranjan Sahoo, Biplab Maji
Summary: In this study, enantioselective C(sp(3))-H bond functionalizations of 2-alkyl azaarenes were achieved using a cooperative dual Lewis acid catalysis, showing good to excellent yields and selectivity across a range of complex molecular scaffolds while accepting a wide variety of functional groups.
Article
Chemistry, Organic
Fei Yu, Chuang Li, Chuangye Wang, Hongwei Zhang, Zhong-Yan Cao
Summary: A new, simple, and easily accessible (1-selenocyanatoethyl)-benzene has been developed and used as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp(3))-H bonds for the first time. The protocol features mild reaction conditions and a wide substrate scope, with control experiments suggesting a radical-group transfer mechanism may be involved.
Article
Chemistry, Organic
Xandro Vidal, Jose Luis Mascarenas, Moises Gulias
Summary: The palladium-catalyzed formal (4 + 2) cycloaddition reaction described in the study offers a direct and unconventional approach to tetrahydroquinoline skeletons through the activation of C(sp(3))-H bonds. The reactivity can also be extended to ortho-methyl benzylamides, allowing for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process.
Article
Chemistry, Organic
Bruce A. L. Sacchelli, Bianca C. Rocha, Leandro H. Andrade
Summary: An ultrafast methodology utilizing microwave irradiation was employed for the first time to construct novel highly functionalized 2-quinolinones from N-(o-ethynylaryl)-acrylamides (1,7-enynes). The method involved six key consecutive reactions, including a diastereoselective step, to achieve good overall yield of 2-quinolinone-fused gamma-lactones (up to 46%; 10 s).
Article
Chemistry, Organic
Chengyu Sun, Yang Yu, Xiao Zhang, Yonghai Liu, Chengtao Sun, Guoyin Kai, Lei Shi, Hao Li
Summary: This study presents a transition-metal-free decarbonylative alkylation reaction for synthesizing N-aryl alpha-hydroxy amides through precise cleavages and reorganizations of three C-C sigma bonds. Additionally, a one-pot inert C-C bond activation/deuteration concept is demonstrated, enabling the formation of alpha,beta-deuterated hydroxyamides using DMSO-d(6) as a solvent.
ORGANIC CHEMISTRY FRONTIERS
(2021)
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.