Article
Chemistry, Organic
Kai-Hong Lv, Qing-Sheng Zhao, Ke-Hua Zhao, Jia-Ming Yang, Sheng-Jiao Yan
Summary: A novel protocol for the synthesis of highly functionalized indolizine derivatives, known as 1H-pyrrolo[3,4-b]-indolizine-1,3-diones (PIZDOs), has been developed through regioselective oxidative [3 + 2] annulation. The cascade oxidative reaction was achieved by heating a mixture of 2-(pyridine-2-yl)acetates and maleimides in the presence of Ag2CO3 and Cu(OAc)center dot H2O catalyst in chlorobenzene. The method allows for the one-pot oxidative annulation reaction to synthesize functionalized PIZDOs instead of multiple steps reactions, making it suitable for both combinatorial and parallel syntheses of PIZDOs.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kexin Su, Xin Guo, Liangwei Zhu, Yafeng Liu, Yixuan Lu, Baohua Chen
Summary: A novel radical cross-coupling/cyclization method has been developed for the straightforward synthesis of structurally diverse methylthio-substituted indolizine compounds. In this process, sulfoxonium ylides undergo disproportionation to produce a new type of indolizine derivative, revealing that DMSO does not drop off from sulfoxonium ylides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Na Kang, Zeng-Xia Zhao, Hong-Xing Zhang
Summary: This study explored the reaction mechanism and formation of C3-substituted indoline derivatives from aniline derivatives containing a pyrimidine-directing group and vinylsilanes. The reaction involves several steps including C-H activation, 2,1-vinylsilane insertion, NH amide proton deprotonation, Ag+ oxidation, and reductive elimination. The insertion of the vinylsilane is not only the critical step for regioselectivity but also the rate-determining step. The computational analysis demonstrates that the Ag+ oxidation can accelerate the reductive elimination step, highlighting the role of Ag+ as a catalytic promoter.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Francis Giraud, Beatrice Josselin, Sandrine Ruchaud, Fabrice Anizon, Pascale Moreau
Summary: The impact of planarity of a heterocyclic system on protein kinase inhibition was studied by synthesizing and evaluating new compounds.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Sayan K. Jana, Mamata Maiti, Purusattam Dey, Biplab Maji
Summary: A facile synthesis method for mono-, 1,1-and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis under mild conditions was demonstrated. Mechanistic inspection and control experiments revealed the importance of dual catalysis and the reaction proceeds via a stepwise oxidative addition followed by an intramolecular S(N)2 reaction.
Article
Chemistry, Organic
Nityananda Ballav, Suman Dana, Mahiuddin Baidya
Summary: The hydrocarbofunctionalization of allyl amines connected to the picolinamide directing group is developed under Pd(II) catalysis. The strategy is based on a nucleopalladation concept and can effectively produce indole derivatives. The synthetic utilities of this reaction, including the Pictet-Spengler cyclization and beta-carboline synthesis, were demonstrated. Mechanistic studies indicate that the reaction proceeds through an irreversible nucleopalladation pathway.
Article
Chemistry, Organic
Nityananda Ballav, Suman Dana, Mahiuddin Baidya
Summary: This study introduces a Pd(II)-catalyzed hydrocarbofunctionalization method for allyl amines connected to the picolinamide directing group. The approach is based on the concept of nucleopalladation and a wide range of indoles effectively participate to produce valuable tryptamine derivatives with high yields. Synthetic utilities are showcased through substrate diversification bearing bioactive core, Pictet-Spengler cyclization, and beta-carboline synthesis. A mechanistic study suggests an irreversible nucleopalladation step, while protodepalladation follows a reversible pathway.
Article
Biochemistry & Molecular Biology
Alexander Aksenov, Nikolai A. Arutiunov, Dmitrii A. Aksenov, Artem Samovolov, Igor A. Kurenkov, Nicolai A. Aksenov, Elena A. Aleksandrova, Daria S. Momotova, Michael Rubin
Summary: Microwave-assisted reaction between 2-(3-oxoindolin-2-yl)-2-phenylacetonitriles and benzene-1,2-diamines leads to the formation of high-yielding quinoxalines as the sole, easily isolatable products. The transformation involves the unusual extrusion of a phenylacetonitrile molecule and can be performed efficiently using readily available indoles and nitroolefins.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Medicinal
Jingbo Qiu, Xiaohui Chen, Weihao Liu, Jun Chen, Weirong Liu, Yongzhen Xia, Zhehui Li, Mingyu Li, Shaojuan Wang, Quan Yuan, Yingkun Qin, Zhen Wu, Meijuan Fang
Summary: In this study, a series of novel Nur77 modulators were designed, synthesized, and evaluated for their anti-cancer activity. Compound 8b exhibited potent activity against various cancer cell lines, including liver cancer cells, with lower toxicity than the positive compound celastrol. Moreover, 8b showed excellent Nur77-binding activity and demonstrated good safety and anti-hepatocellular carcinoma (HCC) activity in vivo.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Boriss Strumfs, Kirils Velikijs, Romans Uljanovs, Stanislavs Sinkarevs, Ilze Strumfa
Summary: This review mainly focuses on recently described or updated ways to obtain 3-arylated aziridines via different non-aziridination-based synthetic methods. These methods primarily include cyclization of open-chain substrates and rearrangement of other heterocycles.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Debabrata Maiti, Atreyee Halder, Aswathy Sasidharan Pillai, Suman De Sarkar
Summary: The mild and efficient electrochemically driven synthetic route allows for the access of polysubstituted selenofuran derivatives through diselenide-promoted cyclization of homopropargyl alcohols, with up to 84% isolated yield. This methodology demonstrates good functional group compatibility and further conversion to valuable furan derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bhanwar Kumar Malviya, Karandeep Singh, Pradeep K. Jaiswal, Manvika Karnatak, Ved Prakash Verma, Satpal Singh Badsara, Siddharth Sharma
Summary: This study reports a catalyst-free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction. Detailed mechanistic studies revealed that the coupling reaction proceeds by the cathodic reduction of in situ formed diazonium ions, which then coupled with isocyanides to furnish the desired products in good yields.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Alla I. Vaskevych, Nataliia O. Savinchuk, Ruslan I. Vaskevych, Svitlana V. Shishkina, Mykhailo V. Vovk
Summary: 2-butenylquinazolin-4(3H)-ones can undergo intramolecular aza-Wacker cyclization to form methylene-substituted pyrrolo(pyrido)[2,1-b]quinazolinones when treated with the catalytic system Pd(OAc)(2)/PPh3/Cs2CO3/benzoquinone in dioxane or Pd(PPh3)(2)Cl-2/t-BuONa/Cs2CO3/benzoquinone in toluene. The latter catalytic system also reacts with pentenyl(hexenyl)quinazolin-4(3H)-ones, but leads to the formation of vinyl-substituted pyrrolo(pyrido)[2,1-b]quinazolinones via competition between aminopalladation of C-H multiple bonds and allylic C(sp(3))-H bond activation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pei-shang Li, Qiao-qiao Teng, Ming Chen
Summary: Described here is a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction between N-aryl acrylamide and vinyl arenes. A variety of bioactive oxindoles with an all-carbon quaternary center were synthesized. The reaction proceeds via an open-shell intermediate and occurs under mild reaction conditions, showing excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (& PLUSMN;)-physostigmine and (& PLUSMN;)-physovenine.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Ming Zeng, Jia-Le Chen, Xue Luo, Yan-Jiao Zou, Zhao-Ning Liu, Jun Dai, Deng-Zhao Jiang, Jin-Jing Li
Summary: We report an efficient copper-catalyzed synthesis of pyridin-2-yl-methanones using water as the oxidant for direct Csp(3)-H oxidation. This method is applicable to pyridin-2-yl-methanes with various aromatic rings and provides moderate to good yields.
Article
Chemistry, Multidisciplinary
Peng Zhang, Xiao-Mei Wang, Qi Xu, Chang-Qiu Guo, Peng Wang, Chuan-Jun Lu, Ren-Rong Liu
Summary: In this study, a Pd-catalyzed cross-coupling strategy was employed for the synthesis of N-C axially chiral biaryl molecules with excellent enantioselectivities and good yields. The practicality of this reaction was demonstrated in the synthesis of biologically relevant molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qi Xu, Huan Zhang, Fang-Bei Ge, Xiao-Mei Wang, Peng Zhang, Chuan-Jun Lu, Ren-Rong Liu
Summary: In this study, we demonstrate that copper(I) catalysis using a bis(phosphine) dioxide ligand can efficiently catalyze the desymmetric C-H arylation of prochiral bipyrroles with excellent enantioselectivities. More than 50 nitrogen-nitrogen atropisomers were achieved in good to excellent yields. The mild reaction conditions and good functional group compatibility on arenes and diaryliodonium salts make this method highly versatile.
Article
Chemistry, Organic
Peng Zhang, Jia Feng, Ren-rong Uu
Summary: Benzimidazole atropisomers with a C-N axis are privileged structural frameworks in pharmaceutical and natural products, and their asymmetric synthesis has attracted increasing attention. This paper briefly discusses recent advances in the asymmetric synthesis of benzimidazole atropisomers with a C-N axis, focusing on the recently developed palladium-catalyzed intramolecular Buchwald-Hartwig amination strategy.
Article
Chemistry, Organic
Wang Yao, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: This study reports a novel method for the enantioselective synthesis of axially chiral 2,2' difluoro-1-biaryls using a palladium and chiral amino acid catalyzed atroposelective C-H olefination. The results demonstrate that a variety of polyfluoro-substituted biaryls can be efficiently synthesized under mild conditions with excellent enantioselectivity.
Article
Chemistry, Multidisciplinary
Chang-Qiu Guo, Chuan-Jun Lu, Li-Wen Zhan, Peng Zhang, Qi Xu, Jia Feng, Ren-Rong Liu
Summary: This study reports a new catalyst that successfully catalyzes the enantioselective coupling reaction between quinone esters and anilines, resulting in the formation of N-aryl quinone atropisomers with a unique intramolecular hydrogen bond. This method has the potential to be used for the synthesis of structurally diverse secondary amine atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Chuan-Jun Lu, Qi Xu, Jia Feng, Ren-Rong Liu
Summary: In the past few decades, the Buchwald-Hartwig reaction has played a vital role in the pharmaceuticals, materials, and catalysis fields as a powerful tool for forming C-N bonds. However, the development of asymmetric Buchwald-Hartwig amination reactions for constructing centered chirality, planar chirality, and axial chirality has been limited due to substrate scope and ligand design challenges. Recent interest in the synthesis of C-N/N-N atropisomers has led to a resurgence in asymmetric Buchwald-Hartwig amination chemistry, providing a practical protocol for the preparation of C-N atropisomers. This review discusses reported protocols and their chemical practicality.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Polymer Science
Bozhen Wu, Renrong Liu, Yuhao Yang, Honghao Zhu, Yujing Yu, Jiang Huang, Yulin Li
Summary: This study develops nickel-coated silicon carbide whiskers/graphene nanosheets/polyvinylidene fluoride composites with an asymmetric structure for high electromagnetic interference shielding capability and absorption efficiency. The composites show different shielding mechanisms when electromagnetic waves are incident from different faces.
JOURNAL OF APPLIED POLYMER SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Wang Yao, Chuan-Jun Lu, Li-Wen Zhan, Yi Wu, Jia Feng, Ren-Rong Liu
Summary: In this study, a palladium-catalyzed enantioselective C-H activation method for pyrroles was reported, which successfully synthesized structurally diverse indole-pyrrole atropisomers with a chiral N-N axis, showing high yields and enantioselectivities. Furthermore, the kinetic resolution of trisubstituted N-N heterobiaryls with more sterically demanding substituents was also achieved. This versatile method enables the rapid and selective functionalization of pyrroles, facilitating the synthesis of valuable and complex N-N atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Peng Zhang, Chang-Qiu Guo, Wang Yao, Chuan-Jun Lu, Yingzi Li, Robert S. S. Paton, Ren-Rong Liu
Summary: A palladium-catalyzed amination method was developed to construct structurally diverse N-C atropisomers, and the reaction mechanism was explained using density functional theory calculations. This method has a broad substrate scope, high stereoselectivity, a simple catalytic system, good functional group tolerance, and dynamic kinetic resolution.
Review
Chemistry, Multidisciplinary
Jia Feng, Chuan-Jun Lu, Ren-Rong Liu
Summary: Atropisomers with rotation-restricted axis are common in natural products, chiral ligands, and drugs, which has led to an increase in asymmetric synthesis. However, the research on N-X atropisomers is not as developed as the C-C atropisomer analogue. N-X atropisomers could offer divergent scaffolds, which are important in bioactive molecules. The asymmetric synthesis of N-X atropisomers is both appealing and challenging.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Li-Wen Zhan, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: This study reports for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons, resulting in the synthesis of chiral C-N atropisomers. The reaction conditions are mild and lead to excellent regio-, stereo- (Z-selectivity), and enantioselectivity. The simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jia Feng, Ren-Rong Liu
Summary: This article summarizes the asymmetric synthesis of N-N biaryl atropisomers and their importance in natural products, drug design, and asymmetric synthesis. The article introduces several synthetic strategies for N-N biaryl atropisomers and offers an outlook for future research.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Huan Zhang, Yi Ding, Mei-Ru Zhang, Chuan-Jun Lu, Jia Feng, Ren-Rong Liu
Summary: Here, the authors report a palladium-catalyzed double C-N coupling reaction between 9H-carbazol-9-amines and 2,2'-dibromo-1,1'-biphenyl. This method provides a route to synthesize N,N'-bicarbazole scaffolds, which are commonly used as linkers in the construction of functional covalent organic frameworks (COFs). The authors successfully synthesized various substituted N,N'-bicarbazoles in moderate to high yields, and demonstrated the potential application of this method in the synthesis of COF monomers like tetrabromide 4 and tetraalkynylate 5.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qi Xu, Chuan-Jun Lu, Chang-Qiu Guo, Jia Feng, Ren-Rong Liu
Summary: This study reports a new palladium-catalyzed rearrangement reaction of VCPs (dienyl or trienyl cyclopropanes) for the construction of functionalized cyclopentene units with high yields and excellent enantioselectivities. The method has significant implications for the synthesis of organic compounds containing cyclopentanes or cyclopentenes.