Article
Chemistry, Applied
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Summary: A product-selective strategy was employed to synthesize benzothiophene-fused polycyclic compounds via a three-component domino reaction. Different substrates led to the formation of different products, impacting the reaction pathway and product structure.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Agriculture, Multidisciplinary
Xiao Zhang, Yiping Wang, Zhiping Xu, Xusheng Shao, Zewen Liu, Xiaoyong Xu, Peter Maienfisch, Zhong Li
Summary: This study demonstrated that converting the pyridyl moiety of IPPA08 into phenyl groups can lead to a new synergist with oxabridged moiety for neonicotinoid insecticides, increasing its toxicity against Aphis craccivora while showing selectivity in its effects on honey bees.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xin-Xin Yang, Ming-Ying Wu, Shao-Qiu Wang, Shang-Dong Yang
Summary: This study reports a transition-metal-catalyzed reaction that allows for the direct functionalization of insert C-H bonds to form carbon-carbon bonds. The reaction proceeds via a unique eight-membered palladacyclic intermediate and demonstrates good compatibility with various functional groups under mild reaction conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Morad M. El-Hendawy, Asmaa M. Kamel, Mahmoud M. A. Mohamed, Rabah Boukherroub, Jacek Ryl, Mohammed A. Amin
Summary: This study evaluated six diaryl sulfide derivatives as potential corrosion inhibitors, finding that five of them may be more effective than dapsone as corrosion inhibitors.
Article
Chemistry, Organic
Seo-Jung Han, Marchello A. Cavitt, Brian M. Stoltz
Summary: An efficient method for the direct synthesis of eight-membered nitrogen-containing heterocycles from secondary and tertiary alcohols was developed. This operationally simple reaction tolerates various functional groups and is applicable to the synthesis of diverse medium-sized ring nitrogen-containing heterocycles.
Review
Chemistry, Organic
Xuan-Chi Yu, Can-Can Zhang, Ling-Tao Wang, Jiao-Zhe Li, Ting Li, Wen-Ting Wei
Summary: Seven- and eight-membered rings are commonly found in natural products and drugs. Their synthesis is challenging due to transition state nonbonding interactions, torsional strains, flexible conformations, and complex multi-ring skeletons. The radical strategy, using metal-induced, oxidant-initiated, electrochemically promoted, or photoinduced systems, offers a powerful tool to overcome the limitations of poor selectivity and harsh reaction conditions. This review highlights recent advances in the synthesis of seven- and eight-membered rings and provides insights into exploring new reaction models in radical chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yotsakorn Saebang, Juthanat Kaeobamrung, Vatcharin Rukachaisirikul
Summary: The straightforward synthesis of quinazolinones with N-fused medium-sized ring urea was achieved, involving key intermediates tert-butyl {2-[4-oxo-2-(4-oxopentyl)quinazolin-3(4H)-yl]ethyl]carbamates derived from copper-catalyzed domino reaction and direct cyclization using 1,1'-carbonyldiimidazole (CDI).
Article
Chemistry, Medicinal
Xiao Zhang, Weiwei Yu, Xiaoyong Xu, Xusheng Shao, Zhong Li
Summary: A serendipitous reaction of introducing nitro group from nitromethylene was observed in the studies on dihydroxy intermediate synthesis. Dinitration structures with nitromethylene analogues were prepared under mild conditions by using a metal-free catalyst B(OH)3, instead of expected dihydroxy compounds. The extra nitro group was suggested to be from starting material.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Applied
Amit Shikari, Koushik Mandal, Deepak Chopra, Subhas Chandra Pan
Summary: A new organocatalytic asymmetric synthesis method has been developed for the synthesis of cyclic acetals with a spirooxindole skeleton. It was found that a bifunctional squaramide catalyst with an adamantyl motif was the most effective in the cascade reaction, providing high diastereo- and enantioselectivities for the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Polymer Science
Xiaoyan Tang, Changxia Shi, Zhen Zhang, Eugene Y-X Chen
Summary: Ring-opening polymerization (ROP) of 7-heptanolactone via metal-catalyzed coordinative-insertion polymerization has been reported, resulting in high-molecular-weight poly(7-hydroxyheptanoate) (P7HHp). Copolymerization with an eight-membered cyclic diester led to the formation of bi-block copolymer P3HB-b-P7HHp with two crystalline domains. The mechanical testing showed that the copolymer exhibited a combination of high modulus and high ductility.
JOURNAL OF POLYMER SCIENCE
(2022)
Article
Chemistry, Inorganic & Nuclear
Thamodharan Viswanathan, Nallasamy Palanisami
Summary: The synthesized borasiloxanes 1 and 2 were characterized by various spectroscopic techniques and single-crystal X-ray diffraction method, with studies on intra-molecular charge transfer and second-order nonlinear optical properties. Compound 2 exhibited 1.5 times higher SHG efficiency than compound 1 due to the presence of ferrocene moiety conjugated in the para position, involving an effective one-electron transfer process. The experimental results of optical and nonlinear optical properties were supported by DFT and TD-DFT calculations using the B3LYP/6-31+G** level of theory.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Si-Jia Yu, Jian-Liang Ye, Ya-Cheng Hong, Pei-Qiang Huang
Summary: This paper describes the construction of functionalized and fused eight-membered carbocycles by triflic anhydride-mediated cyclization of 7-enamides. The reactions proceed smoothly to afford nonconjugated beta,gamma-enimines, conjugated alpha,beta-enimines, or fused 5/8 ring systems in good yields. Acidic hydrolysis of the cyclization reactions leads directly to the corresponding alpha,beta-enones, providing an efficient access to pendent cyclic beta,gamma-enimines/enones for some substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Mateo M. Salgado, Alejandro Manchado, Carlos T. Nieto, David Diez, Narciso M. Garrido
Summary: The passage discusses the mechanism of action of ezetimibe and its analogues in lowering blood cholesterol levels, as well as a convenient synthesis method. The study demonstrates the preparation of compounds with full stereochemical control through a series of reactions and showcases pharmacophore study on drug ligands.
Article
Chemistry, Physical
Wu-Lin Yang, Yuan-Lin Wang, Wen Li, Bu-Ming Gu, Si-Wen Wang, Xiaoyan Luo, Bo-Xue Tian, Wei-Ping Deng
Summary: This study developed an efficient method for synthesizing 8-membered benzo[b]oxocines with high stereocontrol and yield through a sequential catalytic reaction. The chiral iridium catalyst was found to control enantioselectivity, while the chiral bifunctional squaramide catalyst controlled diastereoselectivity. The strategy was also demonstrated to be applicable for synthesizing other nitrogen heterocycles with high enantiomeric enrichment.
Article
Chemistry, Physical
Yasushi Yoshida, Takashi Mino, Masami Sakamoto
Summary: This study reports the design and development of chiral cyclic diarylbromonium salts, enabling highly selective Lewis acid XB catalysis with products reaching up to 96% ee.
Article
Chemistry, Organic
Rongchao Xue, Yongzhu Zhou, Qianghao Lin, Lei Zhang, Chengjie Li, Yu Chen, Yongshu Xie, Xiujun Liu
Summary: Sulfolenopyrrole-based normal and N-confused phlorins were constructed to study the effect of pyrrole linkage modes on the [4 + 2] cycloaddition reaction. The results showed that the confused pyrrole in the N-confused phlorin enabled the rapid formation of a monofullerenoadduct under milder conditions, while the analysis of its structure indicated that fullerene attached to the iminopyrrole part. The high regioselectivity in the [4 + 2] cycloaddition of the imino-type sulfolenopyrrole unit was also supported by density functional theory calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hong-Jing Long, Lei Zhang, Bing Lian, De-Cai Fang
Summary: This study investigated the ruthenium-catalyzed decarbonylative annulation of an alkyne with a hydroxychromone, revealing key steps such as the breaking of C-C bonds and the favorable reaction pathways. The calculations also utilized the steady-state approximation and modified energy span model to determine the apparent activation free energy of the catalytic cycle.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Lei Zhang, Ying Liu, Yongzhu Zhou
Summary: The competition among different pathways in the cycloaddition reactions between isatin azomethine imine and in situ generated azaoxyallyl cation were explored using density functional theory calculations. It was found that the [3+2] cycloaddition between azaoxyallyl cation and carbonyl group can proceed via N-alkylated or O-alkylated pathways to give 4-oxazolidinone or imidate skeleton products, respectively. The exclusive formation of 4-oxazolidinone product is attributed to its higher stability and feasible conversion. The [3+3] reaction between azaoxyallyl cation and azomethine imine was predicted to be less favorable kinetically than the [3+2] reaction. Charge and orbital analyses were performed to explain the observed reactivities of isatin azomethine imine.
Article
Chemistry, Multidisciplinary
Lei Zhang, Ling-Ling Wang, De-Cai Fang
Summary: Density functional calculations were carried out to understand the mechanism of ruthenium-catalyzed C-H allylation. The study reveals the sequential processes involved in the reaction and identifies the rate-determining step as C-H activation. Additional calculations explored other reaction pathways between arenes and alkenes.
Article
Nanoscience & Nanotechnology
Baofa Lan, Xiaoming Wu, Feng Ma, Lei Zhang, Shougen Yin
Summary: In this work, three new SubPc derivatives were designed and synthesized for use in high-performance OPDs. These derivatives exhibited improved intramolecular charge transfer, high electron mobilities, optimized energy levels, and good thermal stability. The SubPc heterojunctions showed a dual-band response and self powered effect, with the optimal OPD outperforming most reported SubPc-based OPDs. The better interfacial contact of the derivatives led to improved device performances.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Jiali Huang, Wenyang Wang, Lei Zhang, Xiangtai Meng
Summary: This review summarizes the latest developments in the construction of benzo[b]thiophene-fused heterocycles by ring formation at the C2-C3-position of benzo[b]thiophene derivatives in the past decade. The review is divided into four parts according to the four kinds of benzo[b]thiophene derivatives used, including thioaurone, thioisatin, substituted benzo[b]thiophene, and azadiene.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Baoxin Wang, Wenhuan Ding, Lei Zhang, Xiangtai Meng
Summary: Novel domino reaction produces a series of PHAs containing sulfur and nitrogen atoms and enables concise synthesis of a new AIEgen. Density functional calculations reveal the role of heteroatom effect in regioselectivity in the reaction mechanism.
Article
Chemistry, Organic
Guixian Liu, Ling-Ling Wang, Yongzhu Zhou, Jianguo Zhou, Lei Zhang
Summary: Density functional theory calculations were used to investigate the reaction mechanism of the twofold C-H annulation of arylformamides with alkynes by Ni-Al bimetallic catalysis. The main pathway involved formyl C-H activation, phenyl C-H activation, migratory insertion, and reductive elimination steps. The annulation product was found to be the equilibrium-controlled product, while the hydrocarbamoylation product was the kinetics-controlled product. The study also highlighted the importance of a bifunctional secondary phosphine oxide ligand in enhancing reactivity and selectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenyang Wang, Ying Wang, Xiaowei Zhao, Wenjiao Yuan, Lei Zhang, Xiangtai Meng
Summary: We developed a NaH-promoted domino reaction between an azadiene bearing an indene moiety and a Nazarov reagent, leading to the synthesis of various substituted spiro[4.5]decane derivatives with good yields and high diastereoselectivity via [4+2] cycloaddition. The reaction conditions are mild and exhibit broad substrate scope. Furthermore, gram-scale experiment and transformation of the product were successfully carried out. Finally, DFT calculations were performed to confirm the proposed reaction mechanism and analyze the observed diastereoselectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Jiali Huang, Lei Zhang, Xiangtai Meng
Summary: Nitrogen- and sulfur-containing heterocyclic compounds are widely found in bioactive natural products and drug molecules. Efforts have been made to develop convenient and efficient strategies for synthesizing these compounds. Pyridinium zwitterions with unique reactivity have played a significant role in the construction of heterocycles. In recent years, these zwitterions have been extensively used in cyclization reactions to synthesize novel heterocyclic compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Baolin Liu, Qingsong Deng, Lei Zhang, Aimin Yu, Xiangtai Meng
Summary: This study reveals the mechanism of the domino reaction of thioisatin with bromoacetophenone and tryptamine hydrochloride, and demonstrates the crucial role of the acid-base form of the amine partner in the selectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuping Song, Gaoting Zhang, Youlai Zhang, Huan Zhang, Xiangtai Meng, Lei Zhang
Summary: This study reports a leaving-group controlled N- or C-cyclization of azadienes, which produces high yields of benzothiophene fused pyrroles or spiro compounds. Density functional calculations reveal the impact of the leaving group on the selectivity of the cyclization reactions. The role of the heteroatom of the azadiene on the reactivity and selectivity is demonstrated by using different azadiene substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Inorganic & Nuclear
Ma Xiao-Si, Zhou Yong-Zhu, Zhang Lei
Summary: Ligands can have a significant influence on C-H activation at the metal center. Univalent ligands and strongly sigma-donating ligands hinder the C-H activation process, while poorly sigma-donating ligands have minimal effects. Ligands trans to the reaction site have a greater impact on C-H activation than those cis to the reaction site.
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Li Zheng, Gu Yingchun, Xu Dazhen, Fei Xuening, Zhang Lei
Summary: In this article, density functional theory calculations were performed on the mechanism of a phosphine-catalyzed cycloaddition reaction. The predicted enantioselectivity results were consistent with experimental findings, and the substituent effects concerning the diene substrate were explored.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Meiyan Liu, Mingkuan Cui, Lei Zhang, Yongkang Guo, Xiaoyang Xu, Wenlong Li, Yuanhao Li, Bin Zhen, Xiaoming Wu, Xuguang Liu
Summary: In this study, a series of bis-BN dipyrrolyl[a,j]anthracenes and a carbonaceous analogue were successfully synthesized. The bis-BN dipyrrolyl[a,j]anthracenes exhibited stronger fluorescence and blue-shifted absorption and emission spectra compared to the carbonaceous analogue. Furthermore, organic light-emitting diodes based on these compounds showed high efficiency and pure-blue emitting color.
ORGANIC CHEMISTRY FRONTIERS
(2022)
