Article
Chemistry, Organic
Jiaxin Liu, Yin Wei, Min Shi
Summary: A new method for the direct single-electron oxidation of methylenecyclopropanes (MCPs) was reported, leading to the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives through merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N·3HF, fluorinated derivatives were obtained in moderate yields, while in MeCN/HFIP, good yields were achieved through a MHAT process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yan-Zhi Liu, Yao-Fu Zeng, Bing Shu, Yi-Chuan Zheng, Lin Xiao, Shao-Yong Chen, Jia-Lin Song, Xuanxuan Zhang, Shang-Shi Zhang
Summary: This study describes a Rh(iii)-catalyzed C-H functionalization of indoles at the C4 position using alkylidenecyclopropanes (ACPs). By choosing different ACPs as reactants, diene or cyclopropane motifs can be selectively introduced into indoles. The protocol exhibits excellent regioselectivity and broad substrate scope. Scale-up experiments and mechanistic studies were conducted.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Baoxiang Zhu, Zhao Wang, Hui Xi, Zengqiang Feng, Binglei Wang, Wenyang Jiao, Zhongxian Li, Zechao Wang, Junliang Wu
Summary: A new synthetic method has been developed for the synthesis of various compounds via visible-light-promoted radical monofunctionalization and difunctionalization of methylenecyclopropanes. The reaction conditions are simple and convenient, with moderate to excellent yields, a wide substrate scope, and tolerance for different functional groups. The possible radical mechanism has been investigated and proven to be a single electron transfer (SET) procedure.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Asim Maity, Pritam Roychowdhury, Roberto G. Herrera, David C. Powers
Summary: The study demonstrates that N-benzylaminopyridinium species can provide a platform for synthetic elaboration through reductive N-N bond activation, resulting in the formation of electrophilic N-centered radicals. These reactive intermediates can be further transformed into tetrahydroisoquinolines and alpha-amino ketones via different reactions.
Article
Chemistry, Organic
Mingdong Jiao, Xianjie Fang
Summary: A novel synthesis of homoallylic nitriles via cobalt-catalyzed hydrocyanation of methylenecyclopropanes is described. The protocol demonstrates excellent selectivity, mild reaction conditions, good functional group compatibility, gram-scale reaction, and product transformations. The extraordinary selectivity is probably attributed to the stronger aptitude of the alkyl-cobalt cyanide intermediate for reductive elimination rather than beta-hydride elimination.
Article
Chemistry, Organic
Louis G. Mueller Jr, Taylor M. Keller, Fraser F. Fleming
Summary: Substituted oxazoles and imidazoles can be synthesized in one pot using the isocyanide building block Asmic, an alkyl halide, and an acid chloride or nitrile. The modular assembly involves sequential deprotonation-alkylation and deprotonation-acylation or imination of Asmic, followed by a unique carbon-sulfur bond cleavage to construct the azole. This strategy is robust, highly efficient, and allows for the formation of C4-C5 disubstituted oxazoles or imidazoles in a single operation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Lei Zhan, Lei Gao, Ying-Ming Pan, Mu-Xue He, Xian-Li Ma, Zu-Yu Mo
Summary: This study presents an approach for the electrochemical oxidation ring-opening/cyclization reaction of methylcyclopropane with diselenides/ditellurides, leading to the synthesis of diverse 2-substituted-3,4-dihydronaphthalene derivatives with exceptional selectivity and efficiency. One characteristic of this method is its ability to accommodate a wide range of substrates with various functional groups.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Shuang Yang, Xiao-Bin Liu, Si-Xin Feng, Yin Li, Fang-Hai Tu, Bin Huang, Long-Ling Huang, Zhi-Shu Huang, Honggen Wang, Qingjiang Li
Summary: This study presents a new method for the synthesis of difluorinated alkylidenecyclobutanes through a hypervalent iodine(iii)-mediated reaction using commercially available Olah's reagent as the fluorine source. The reaction proceeds under mild conditions and provides moderate to good yields. Mechanistic investigations indicate that the reaction involves regioselective 1,2-fluoroiodination of a triple bond followed by a Wagner-Meerwein-type rearrangement.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Suo Chen, Yizhi Zhang, Shanshan Liu, Xiao Shen
Summary: We report the invention of a novel carbene precursor, (1-diazo-2,2,2-trifluoroethyl)dimethyl(phenyl)silane (1a) and its application in the synthesis of (difluoromethylene)cyclopropanes. The reaction proceeds through photocatalyzed [2+1] cyclization of readily available alkenes and diazo compound 1a followed by the work-up of the reaction through the elimination of silyl fluoride. Both aromatic and aliphatic alkenes are tolerated by the mild reaction conditions, affording various (difluoromethylene)cyclopropanes in 44%-82% yield (>30 examples). The synthetic potential of this methodology is highlighted by gram scale reaction and diversified downstream transformations. Experimental and DFT calculations suggest the involvement of triplet carbene intermediate.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Li-Miao Yang, Hui-Hui Zeng, Xin-Lian Liu, Ai-Jun Ma, Jin-Bao Peng
Summary: A copper-catalyzed borocarbonylation reaction has been developed for the synthesis of gamma-boryl-gamma,delta-unsaturated carbonyl compounds. This reaction shows excellent regio- and stereoselectivity and allows for the preparation of a broad range of products. The reaction can be controlled by using different starting materials.
Article
Chemistry, Multidisciplinary
Hui-Qing Geng, Xiao-Feng Wu
Summary: In this study, we have developed a copper-catalyzed hydroaminocarbonylation of benzylidenecyclopropanes under relatively mild conditions. A series of gamma,delta-unsaturated amides with a broad range of functional groups were obtained in moderate to good yields. Both dialkyl-substituted and monoalkyl-substituted hydroxylamine derivatives can be applied in this transformation to give the corresponding tertiary and secondary amides successfully.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Carla Rizzo, Sara Amata, Ivana Pibiri, Andrea Pace, Silvestre Buscemi, Antonio Palumbo Piccionello
Summary: The incorporation of fluorine atoms or heterocyclic moieties into drug structures is a common pattern in medicinal chemistry. The combination of these two features is consistently observed in newly synthesized molecular entities with diverse biological activities, as evidenced by the increasing number of Fluorinated heterocyclic compounds approved by the FDA as drugs. This review highlights the biological activity and synthetic aspects of 33 recently FDA-approved fluorinated heterocyclic drugs from 2016 to 2022.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Multidisciplinary Sciences
Xuan Liu, Bo Li, Guanqun Han, Xingwu Liu, Zhi Cao, De-en Jiang, Yujie Sun
Summary: The synthesis of heterocyclic moieties pertaining to biologically active molecules from biomass-based starting compounds is attractive yet underexplored. In this study, an electrocatalytic Achmatowicz reaction for the synthesis of hydropyranones from biomass-derived furfuryl alcohols was reported.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Javier Garcia-Dominguez, Marina Carranza, Edijs Jansons, Ana T. Carmona, Inmaculada Robina, Antonio J. Moreno-Vargas
Summary: This paper presents the use of 7-oxa/azanorbornadienes as synthetic intermediates for the preparation of 3/4-substituted furans/pyrroles. The method involves the inverse electron demand Diels-Alder (iEDDA) cycloaddition and retro-Diels-Alder (rDA) reactions, resulting in the synthesis of beta-substituted furans/pyrroles. The study explores the application of this method in the preparation of 29 heterocycles and proposes a one-pot procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Hao-Zhao Wei, Yin Wei, Min Shi
Summary: A cascade cyclization method using Weinreb amide-tethered methylenecyclopropanes and alkynes is disclosed in this paper, which extends the umpolung ring opening of methylenecyclopropanes and provides a synthetic approach for constructing polycyclic cyclopenta[b]naphthalenol framework.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Mingxuan Liu, Yiming Li, Lei Yu, Qing Xu, Xuefeng Jiang
SCIENCE CHINA-CHEMISTRY
(2018)
Article
Nanoscience & Nanotechnology
Ming-Xuan Liu, Le-Le Ma, Xu-Ying Liu, Jin-Yu Liu, Zhong-Lin Lu, Rui Liu, Lan He
ACS APPLIED MATERIALS & INTERFACES
(2019)
Article
Chemistry, Multidisciplinary
Mingxuan Liu, Xiaoling Zhang, Sainan Chu, Yanyu Ge, Tao Huang, Yonghong Liu, Lei Yu
Summary: A technique using in situ prepared NaHSe for selenization reaction in aqueous solution has been successfully developed. This method provides a way to incorporate bioactive selenium onto cotton products on a semi-industrial scale. Antibacterial tests showed that selenized cotton exhibited potent and prolonged antimicrobial effects against both Gram-positive S. aureus and Gram-negative E. coli bacteria. This study reveals a practical method for preparing selenium-containing antibacterial materials with industrial application potential.
CHINESE CHEMICAL LETTERS
(2022)
Article
Materials Science, Multidisciplinary
Ming-Xuan Liu, Jia-Ying Zhang, Xiao-Ling Zhang
Summary: Graphitic polymeric carbon nitride (g-C3N4), as a unique material with its unique element composition and photoelectric features, has attracted great interest in the field of biomedicine. g-C3N4, composed only of carbon and nitrogen, exhibits outstanding biocompatibility, making it suitable for applications in biological imaging, antibacterial materials, and photodynamic therapy. This review systematically examines the preparation methods of g-C3N4, its latest developments in biomedical applications, and discusses its biological safety, challenges, and prospects. It is expected that g-C3N4 will be recognized for clinical applications in the near future.
MATERIALS CHEMISTRY AND PHYSICS
(2022)
Article
Biotechnology & Applied Microbiology
Ming-Xuan Liu, Li Xu, Jia-Yi Jiang, Hai-Chen Dong, Peng-Fei Zhu, Lei Cao, Jing Chen, Xiao-Ling Zhang
Summary: The study proposes the concept of self-escape non-cationic gene carriers for targeted delivery and treatment of hepatocellular carcinoma (HCC) using graphitic carbon nitride nanosheets. These nanocomplexes actively target HCC tissue and disrupt lysosome structure to facilitate their escape. They also promote reversible release of DNA in the acidic microenvironment of HCC tissue and effectively upregulate tumor suppressor protein P53 expression for gene therapy of HCC.
BIOENGINEERING & TRANSLATIONAL MEDICINE
(2023)
Article
Engineering, Biomedical
Ming-Xuan Liu, Li Xu, Yu-Ting Cai, Ruo-Jia Wang, Ying-Ying Gu, Yan-Chao Liu, Yu-Jin Zou, Yong-Mei Zhao, Jing Chen, Xiao-Ling Zhang
Summary: This study established a safe and effective method to downregulate the expression of HIF-1 alpha in hepatic stellate cells (HSCs) and treat liver fibrosis. By delivering HIF-1 alpha small interfering RNA (HIF-1 alpha-siRNA) via VA-PEG-modified CNs-based nanosheets encapsulated with GQDs, the expression of HIF-1 alpha can be decreased. Additionally, the nanosheets can trigger water splitting under near-infrared (NIR) irradiation, improving the hypoxic liver fibrosis site and achieving better therapeutic effects.
ADVANCED HEALTHCARE MATERIALS
(2023)
Article
Materials Science, Biomaterials
Ming-Xuan Liu, Li Xu, Peng-Fei Zhu, Xin Li, Miao Shan, Wei Jin, Jing Chen, Yong Ling, Xiao-Ling Zhang
Summary: Researchers successfully synthesized a fluorescent probe DPABP-BI that can identify lipid droplets (LDs) and track their autophagy process. The probe features red fluorescence emission, large Stokes shift, two-photon excitation, outstanding photostability, and biocompatibility. LDs can be specifically identified through the red fluorescence emission of DPABP-BI, while autophagolysosomes can be visualized through the green fluorescence emission of its acid-hydrolyzed product to track the autophagy dynamic process. Additionally, DPABP-BI enables the specific recognition of fatty substances in zebrafish larvae.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
Article
Materials Science, Biomaterials
Ming-Xuan Liu, Xiao-Ling Zhang, Jing-Bo Yang, Zhong-Lin Lu, Qi-Tao Zhang
Summary: Highly water-dispersible polymeric carbon nitride (PCN) nanosheets were used as the core to construct a light-controlled non-cationic gene delivery system with efficient lysosomal escape ability and high transfection efficiency. In vitro and in vivo experiments demonstrated the potential of this system in tumor gene therapy.
JOURNAL OF MATERIALS CHEMISTRY B
(2022)
Article
Nanoscience & Nanotechnology
Ming-Xuan Liu, Xu-Ying Liu, Jin-Yu Liu, Jin-Tao Tang, Ke Shi, Jie Mao, Zhong-Lin Lu, Hai-Jun Qiao, Lan He
Summary: This study reports the design and synthesis of four dendrite-shaped cationic liposomes with efficient DNA condensation, pH-responsive degradation, excellent cellular biocompatibility, and high transfection efficiency. The liposomes demonstrated fast access to the nucleus, successful gene delivery, and trackable intracellular delivery and release of DNA in real time via fluorescence imaging. The results suggest the potential of biomimetic chromophores for the development of next-generation nonviral gene vectors.
ACS APPLIED BIO MATERIALS
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
