Article
Chemistry, Organic
Kangdong Mo, Xiaocong Zhou, Ju Wu, Yufen Zhao
Summary: A robust and green electrochemical method was developed for the dearomatization of indoles, where a fluorine-containing group was merged with an indole nucleus under oxidant-free conditions, resulting in the synthesis of a diverse array of tri- and difluoromethylated 3,3-spiroindolines with good functional group tolerance.
Article
Chemistry, Organic
Ya-Ping Wang, Xing-Ping Zhang, Ming-Sheng Xie, Hai-Ming Guo
Summary: In this study, highly enantioselective propargyl Claisen rearrangement of O-propargyl beta-ketoesters was achieved using a chiral cobalt complex as the catalyst under mild reaction conditions. A diverse range of chiral allenyl-substituted all-carbon quaternary beta-ketoesters were obtained in good yields and high enantioselectivities.
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Gang Wang, Ran Lu, Chuangchuang He, Lei Liu
Summary: The study discusses the challenges and methods of catalytic kinetic resolution of amines, specifically focusing on the titanium-catalyzed asymmetric oxygenation with hydrogen peroxide. This approach allows for the efficient production of enantiopure hydroxylamines from secondary amines, demonstrating high chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules is also explored in this research.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Qing-Xia Zhang, Qing Gu, Shu-Li You
Summary: A Pd-catalyzed intermolecular allylic dearomatization reaction was developed for substituted beta-naphthol derivatives with Boc-protected Morita-Baylis-Hillman adducts. The reaction exhibited high yields and enantioselectivity under mild conditions, making it synthetically useful.
Article
Chemistry, Organic
Qing-Xia Zhang, Qing Gu, Shu-Li You
Summary: The Pd-catalyzed intermolecular asymmetric allylic dearomatization reaction has been developed, showing moderate to excellent yields and enantioselectivity. The compatibility with gram-scale reactions and mild conditions make this method synthetically useful.
Article
Chemistry, Organic
Lemao Yu, Senhao Huang, Tao Cai, Kui Du, Chunlei Wu, Huaping Dong, Runpu Shen
Summary: In this study, a novel compound, triazolo[1,2-a]indoline, was synthesized successfully by the oxidative cyclization between NH-indoles and azomethine imines under metal-free and mild conditions. This finding provides a rapid approach for the tri-functionalization of NH-indoles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guo-Qing Jiang, Bin-Hong Han, Xian-Peng Cai, Jian-Ping Qu, Yan-Biao Kang
Summary: An iron-catalyzed direct aerobic alpha,beta-dehydrogenation of carbonyls has been reported using tert-butyl nitrite and N-hydroxyphthalimide as the co-catalyst system. This method allows for the production of a wide range of lactams, flavanones, lactone, and thiochromen-4-one in high yields without the need for extra transition metal reagents.
Article
Chemistry, Organic
Dengyang Zhao, Yingjie Pan, Shengkun Guo, Xiaoyun Chen, Hong Hou, Ying Han, Chaoguo Yan, Yaocheng Shi, Shaoqun Zhu
Summary: This study describes a copper-catalyzed efficient oxidative dearomatized functionalization of indoles using alcohols as nucleophiles. Various 3-alkoxy-2-oxindoles were synthesized with good isolated yields. The synthetic potential of the reaction was demonstrated through large-scale reactions and derivatization of the desired products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jun Shi, Rui-An Wang, Wei Wu, Jun-Rong Song, Qin Chi, Wei-Dong Pan, Hai Ren
Summary: This study reports a safe and convenient copper-catalyzed selective oxidation method using atmospheric oxygen as the oxidant. The method allows for the oxidative rearrangement of indole compounds, leading to the formation of various functionalized products. This represents a significant advance in the field of indole oxidation.
Article
Chemistry, Organic
Jiamin Lu, Ruigang Xu, Haixia Zeng, Guofu Zhong, Meifang Wang, Zhigang Ni, Xiaofei Zeng
Summary: Iridium/Bronsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields and enantioselectivities with wide functional group tolerance. The transformations not only enable the formation of C5-allylindoline derivatives, but also the synthesis of C5-allylindole analogues in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.
Article
Chemistry, Organic
Chuan-Hua Qu, Shu-Ting Li, Jian-Bo Liu, Dian-Yong Tang, Zhi-Gang Xu, Zhong-Zhu Chen, Gui-Ting Song
Summary: This study achieved the efficient synthesis of diverse benzoazepinespiroindolenine derivatives. The method exhibits excellent chemoselectivity and diastereoselectivity, allowing for the cost-effective introduction of functionality and complexity. The dearomatization of complex Ugi adducts addresses chemoselectivity issues and complements classical methods. The reaction mechanism and chemoselectivity origins were elucidated using density functional theory calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yang Li, Lijun Li, Changyou Guo, Qinqin Yan, Hongxun Zhou, Ying Wang, Zhong-Quan Liu, Zejiang Li
Summary: A metal/peroxide-free cascade reaction involving the 6exo-trig spirocyclization of tert-butyl nitrite with biaryl ynones has been successfully accomplished, leading to various NO2-modified spiro[5,5]trienones with high regioselectivity and yields. Scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were conducted to confirm the advantages and spirocyclization process of this radical system. The structure of the spirocycles was ultimately confirmed by single-crystal X-ray diffraction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chuan-Hua Qu, Shu-Ting Li, Jian-Bo Liu, Dian-Yong Tang, Zhi-Gang Xu, Zhong-Zhu Chen, Gui-Ting Song
Summary: A efficient palladium-catalyzed post-Ugi dearomative cyclization was developed for the rapid synthesis of diverse benzoazepinespiroindolenine derivatives. This methodology offers excellent chemoselectivity and good diastereoselectivity, and provides a cost-effective and step-economical approach for introducing functionality and complexity into dearomatized alicyclic products. The precise dearomatization of complex Ugi adducts resolves challenging chemoselectivity issues and complements classical dearomatization protocols in terms of functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Lingbo Han, Xin Wei, Yi Yuan, Lu Bai, Hui Wang, Xinjun Luan
Summary: In this study, a palladium-catalyzed C-H arylation/arene dearomatization reaction was performed in a redox-neutral manner. This domino reaction involved in situ-formed Pd(II) species, phenolic-group-directed C-H activation, biaryl cross-coupling, and naphthol dearomatization, leading to the rapid assembly of spiro[4,5]fluorenes with high yield and good chemoselectivity. Interestingly, the malononitrile-derived spirofluorene 6 showed mechanoresponsive luminescence and its potential application in optical memory devices.
Article
Chemistry, Organic
Cheng Wang, Guangyang Xu, Ying Shao, Shengbiao Tang, Jiangtao Sun
Article
Chemistry, Multidisciplinary
Kai Wang, Jianliang Yu, Ying Shao, Shengbiao Tang, Jiangtao Sun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Xiaofeng Liu, Ying Shao, Jiangtao Sun
Summary: A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, providing N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to this unprecedented reaction is the use of CpRu(PPh3)(2)Cl as the catalyst and sulfoxonium ylides as the alkylation reagents, which can also be applied to 7-azaindoles with slight variations in reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents for good selectivity in N-alkylation of 2-pyridones.
Article
Chemistry, Organic
Yong Xu, Jiangtao Sun
Summary: This study describes the use of gold-catalyzed cascade cyclization and 1,3-difunctionalization of 2-(1-alkyny)-2-alken-1-ones with N,O-acetals, leading to the discovery of novel 1,3-oxyaminomethylation and 1,3-aminomethylamination. By varying reaction conditions, particularly the gold catalysts, these two distinct reaction pathways can be selectively controlled. Tandem cyclization and 1,4-oxyaminomethylation have also been achieved.
Article
Chemistry, Organic
Ziyong Li, Jiangtao Sun
Summary: This reaction allows for the preparation of trisubstituted alkenylboronates through a copper-catalyzed three-component reaction, selectively occurring at the terminal carbon atom and proceeding through a complex tandem sequence. The copper catalyst plays a crucial role in the process by facilitating both the initial cross-coupling and the subsequent stereoselective boration reaction, with different carbene precursors leading to Z- and E-alkenes selectively.
Article
Chemistry, Multidisciplinary
Kai Wang, Ziye Liu, Guangyang Xu, Ying Shao, Shengbiao Tang, Ping Chen, Xinhao Zhang, Jiangtao Sun
Summary: Asymmetric carbene insertion reactions are crucial for constructing carbon-heteroatom bonds, but high enantioselectivity typically requires the use of donor-acceptor diazo compounds with an ester group. This study presents the first chemo and enantioselective formal N-H insertion of 2-pyridones using enynones as donor-donor carbene precursors, with DFT calculations revealing an unprecedented enantioselective 1,4-proton transfer from O to C. The rhodium catalyst's chiral pocket, along with steric repulsion and pi-pi interactions of the propeller ligand, play essential roles in determining the selectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Guangyang Xu, Zhen Wang, Ying Shao, Jiangtao Sun
Summary: An enantioselective copper-catalyzed tandem cross-coupling/alkynylogous aldol reaction has been developed, yielding tetrasubstituted allenoates with central and axial chirality. This protocol utilizes copper(II) salts as a catalytic precursor, distinguishing it from previous methods using Cu(I) salts.
Article
Chemistry, Organic
Yong Xu, Zhen Wang, Jiangtao Sun
Summary: The study demonstrates the enantioselective [3 + 1]-cycloaddition of two structurally different diazo compounds using chiral bisoxazoline copper(I) complexes as catalysts, leading to a novel route for the synthesis of cyclobutenes with a quaternary stereocenter. This reaction is the first example of asymmetric cross-electrophile coupling of two diazo substrates via carbene discrimination.
Article
Chemistry, Multidisciplinary
Kai Liu, Tingrui Li, Duan-Yang Liu, Weipeng Li, Jian Han, Chengjian Zhu, Jin Xie
Summary: This study reports an unprecedented C-H bond functionalization of cyclopropenes enabled by dinuclear gold catalysis, resulting in highly selective C-H allylation, alkynylation, and halogenation reactions with organic halides. The reaction does not require strong external oxidants and affords access to functionalized cyclopropenes in moderate to good yields. The reductive elimination process for construct C-C or C-X bonds can be controlled by using different dinuclear gold catalysts.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ziyong Li, Ying Chen, Chuang Wang, Guangyang Xu, Ying Shao, Xinhao Zhang, Shengbiao Tang, Jiangtao Sun
Summary: The atroposelective synthesis of biaryl atropisomers via asymmetric C(sp(2))-H bond insertion reaction of arenes under rhodium catalysis has been achieved, providing moderate to excellent yields with good enantiomeric ratios. Further investigation suggests that this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xiaozhou Xie, Jiangtao Sun
Summary: The catalyst-free reaction described in this study allows for the straightforward synthesis of 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions, with a broad substrate scope and good functional group tolerance. Additionally, a series of pyridoazepinones have been prepared using N-pyridinyl sulfilimine as the substrate.
Article
Chemistry, Organic
Jiahui Su, Qiongya Li, Ying Shao, Jiangtao Sun
Summary: An enantioselective cyclopropanation reaction of N-substituted 2-pyridones with diazo compounds has been successfully achieved using a chiral rhodium complex as the catalyst, leading to the formation of chiral cyclopropanes with high enantioselectivities and good yields. Additionally, a novel 1,4-rearrangement of a Boc group from N to C has been discovered under rhodium catalysis when using acceptor-acceptor dimethyl 2-diazomalonate as the carbene precursor.
Article
Chemistry, Organic
Guangyang Xu, Meirong Huang, Tao Zhang, Ying Shao, Shengbiao Tang, He Cao, Xinhao Zhang, Jiangtao Sun
Summary: In this study, an enantioselective insertion of a carbene into the Csp2-H bond of anisole derivatives was achieved using a chiral gold complex and a chiral phosphoric acid as the catalytic system, offering a novel approach for the synthesis of chiral α,α-diarylacetates.
Article
Chemistry, Multidisciplinary
Shengbiao Tang, Peng Zhang, Changkai Wang, Ying Shao, Jiangtao Sun
Summary: The report introduces a new iridium-catalyzed reaction with free carboxylic acids as nucleophiles for synthesizing chiral compounds from racemic secondary allylic alcohols. This method shows excellent regio- and enantioselectivity under mild conditions, allowing for a broad functional group tolerance.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Wenliang Wang, Cheng-Long Ji, Kai Liu, Chuan-Gang Zhao, Weipeng Li, Jin Xie
Summary: This article discusses the recent progress in organic synthesis of dinuclear gold-catalysis, highlighting the particular properties and advantages of dinuclear gold complexes. It summarizes the recent achievements of dinuclear gold-catalyzed coupling reactions, asymmetric catalysis, and photocatalysis.
CHEMICAL SOCIETY REVIEWS
(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.
