Article
Chemistry, Organic
Jeremy Nugent, Alistair J. Sterling, Nils Frank, James J. Mousseau, Edward A. Anderson
Summary: Bicyclo[1.1.1]pentanes (BCPs) are synthesized efficiently using organophotoredox and hydrogen atom transfer catalysis, allowing for the preparation of alpha-quaternary BCPs. The products can be further transformed into a variety of useful derivatives, including enantioenriched BCPs.
Article
Chemistry, Multidisciplinary
Manju Devi, Amol P. Jadhav, Ravi P. Singh
Summary: The stereoselective synthesis of 3,3'-disubstituted oxindoles with all-carbon quaternary stereocenters using KOH as a base has been achieved with an excellent diastereomeric ratio of 98:2. The practicality of the methodology has been demonstrated through the synthesis of a series of substrates with good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly nature of the base (KOH) have led to the broader application of this methodology in organic synthesis.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaoyi Li, Zihao Li, Rong Zhang, Zhen Zhou, Yonghui Zhang, Yi Xia, Weijun Yao, Zhen Wang
Summary: An organocatalyzed stereoselective domino reaction for the synthesis of multicyclic spirooxindole derivatives bearing two stereogenic quaternary carbon atoms is reported. The chiral thiourea catalyst with alkyl substitution efficiently tolerates a wide range of substrates, yielding spirooxindole derivatives with an O,O-acetal-fused tricyclic skeleton or tetrahydroxanthone moiety in moderate to good yields and excellent selectivities. The products generated from this method show promising anticancer activities.
Article
Chemistry, Organic
Xin Hu, Qiang Bian, Zheng-Lin Wang, Lin-Jie Guo, Yi-Ze Xu Ge Wang, Da-Zhen Xu
Summary: A four-component reaction strategy has been developed for access to acyclic nitrile-substituted all-carbon quaternary centers efficiently. By using DABCO-based ionic liquid catalyst, the reactions proceed smoothly under mild conditions, with water as the only byproduct. Some of the products exhibit excellent activity against specific fungi.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaoguang Pan, Min Cao, Song Li, Hengshan Wang, Xigong Liu, Lei Liu
Summary: An efficient construction of diarylmethanes containing CF3- and CN-substituted all-carbon quaternary stereocenters has been achieved via cyanation of delta-CF3-delta-aryl disubstituted para-quinone methides. The method shows broad scope, high efficiency, and enables rapid access to valuable CF3-substituted di- and triarylmethanes. Additionally, cyanation of delta-CN-substituted para-quinone methides furnishes diarylmalononitriles in good yields, demonstrating the generality of the approach.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Weiping Zhou, Arnaud Voituriez
Summary: A cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads to the formation of cyclopentenones with a C4-quaternary stereocenter after cyclization. This methodology was successfully applied to the efficient total synthesis of five natural sesquiterpenoids, demonstrating moderate to good yields and excellent enantiomeric excesses in 26 examples.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Jian Xu, Runze Li, Nian Xu, Xiaohua Liu, Fei Wang, Xiaoming Feng
Summary: The study describes the asymmetric catalytic synthesis of 3-cyclotrypt-amine substituted oxindoles with potential anticancer activity. This strategy allows for the quick assembly of cyclotryptamine subunits with two quaternary stereogenic centers in cis-selectivity.
Article
Chemistry, Organic
Yu Qiao, Shiming Bai, Xiao-Feng Wu, Ying Yang, He Meng, Jialin Ming
Summary: This study discovered that the desymmetric arylation of prochiral cyclohexadienones with ArZnCl in the presence of an (R)-segphos-rhodium catalyst can yield cyclohexenones with a chiral arylated carbon center and a chiral all-carbon quaternary center with high selectivity. The catalytic system is also applicable to the arylation of spirocarbocyclic cyclohexadienones, producing cyclohexenones with a chiral spiro quaternary carbon.
Article
Chemistry, Organic
Sheng Zuo, Yuan Tao, Zhigang Liu, Ke Zhang, Luyun Zhang, Yingtang Ning, Fen-Er Chen
Summary: This study successfully synthesized highly congested indanone-based spirolactones through copper-catalyzed decarboxylative propargylation, with the key role of DPEN-based ligands. The method tolerated a wide range of functional groups, yielding high diastereo- and enantioselectivities. Mechanistic observations indicated the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
Article
Chemistry, Multidisciplinary
Xu-Dong Hu, Zi-Hao Chen, Jing Zhao, Rui-Ze Sun, Hui Zhang, Xiaotian Qi, Wen-Bo Liu
Summary: This research presents an efficient enantioselective Pd(II)-catalyzed cascade reaction for the transformation of alkyne-tethered malononitriles into alpha-quaternary carbazolones with high enantioselectivities. The utility of this method is demonstrated by the synthesis of diverse heterocycles and a nitrile-containing leucomidine A analog from the obtained products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Sijing Xue, Alexander Lucht, Jordi Benet-Buchholz, Arjan W. Kleij
Summary: The challenging metal-catalyzed asymmetric synthesis of highly functional quaternary carbon centers using decarboxylative C(sp(3))-C(sp(3)) bond formation reactions has been successfully reported in this study. By activating a key substrate, a vinyl cyclic carbonate, both the requisite nucleophile and electrophile reaction partner were provided for the asymmetric cross-coupling process. Through extensive screening of reaction conditions, additives and catalyst precursors, a protocol was developed that allowed access to a series of compounds featuring densely functionalized, elusive quaternary carbon stereocenters in appreciable yield and with enantiomeric ratios (er's) of up to 90 : 10.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Zhengyuan Xin, Hui Wang, Haibing He, Shuanhu Gao
Summary: This paper focuses on the importance of contiguous all-carbon quaternary centers in natural products and recent synthetic strategies used in total syntheses. By reviewing 12 representative synthetic examples, the power of these reactions in constructing such centers is showcased to inspire future exploration.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Oceane Flores, Patrick Wagner, Jean Suffert
Summary: Exploration of 4-exo-dig cyclocarbopalladation in the discovery of new and original scaffolds resulted in unexpected findings, including the identification of polycyclic molecules with a tetrasubstituted carbon. The presence of a triple bond substituting the cyclohexene ring on the starting compound was found to be crucial for high stereoselectivity. This observation was confirmed by the reaction of a nonsubstituted cyclohexene ring, which led to poor stereoselectivity and low yields.
Article
Chemistry, Organic
Morgane Mando, Mathieu Fares, Christelle Kowandy, Fabienne Grellepois, Emmanuel Riguet
Summary: In this study, the synthesis of enantioenriched alpha-aryl-alpha'-allyl-gamma-butyrolactones bearing vicinal tertiary and quaternary stereocenters through organocatalyzed asymmetric allylic alkylation was reported.
Article
Chemistry, Multidisciplinary
Haoran Dong, Dachao Hu, Benke Hong, Jin Wang, Xiaoguang Lei
Summary: The first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, featuring a tetramic acid bearing cis-decalin ring, are reported. The functionalized cis-decalin ring was constructed via a diastereoselective intramolecular Diels-Alder (IMDA) reaction, with a rare endo-boat transition state. The efficient installation of the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A, and AB4015-L was achieved through an intramolecular neighboring-group-oriented strategy, and the desired tetramic acid structure was obtained through a one-pot aminolysis/Dieckmann condensation cascade using L-amino acid derivatives. The total synthesis allowed for the unequivocal verification of the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Chunlin Ye, Xujian Chen, Shasha Li, Binbin Feng, Yanghe Fu, Fumin Zhang, De-Li Chen, Weidong Zhu
Summary: Enhancing the selectivity of noble metal catalysts through electronic modulation is crucial for academic research and chemical industrial processes. The developed PdZn-ZnO/NCHS catalyst shows excellent catalytic performance for the semihydrogenation of 2-methyl-3-butyn-2-ol, with high activity and selectivity.
Article
Oncology
Yunxiao Liu, Yuliuming Wang, Hao Zhang, Mingyu Zheng, Chunlin Wang, Zhiqiao Hu, Yang Wang, Huan Xiong, Hanqing Hu, Qingchao Tang, Guiyu Wang
Summary: The purpose of this study was to explore the risk factors for synchronous liver metastasis (LM) of colorectal cancer (CRC) and construct a nomogram for predicting the occurrence of synchronous LM. The nomogram showed good discrimination and calibration in predicting synchronous LM, providing valuable guidance for screening and treatment decisions.
WORLD JOURNAL OF SURGICAL ONCOLOGY
(2022)
Article
Chemistry, Physical
Wenting Lin, Yaping Song, Li Wang, Nan Li, Yanghe Fu, De-Li Chen, Weidong Zhu, Fumin Zhang
Summary: In this study, Pd/Ce-MOF-801 catalyst was prepared using an incipient wetness impregnation strategy and its physicochemical properties were investigated. The results showed that Pd/Ce-MOF-801 exhibited high catalytic performance in the Suzuki-Miyaura cross-coupling reaction and had good recyclability and tolerance to various substrates.
Article
Environmental Sciences
Yuexian Du, Guang'an Jie, Huilin Jia, Jiahui Liu, Jieyu Wu, Yanghe Fu, Fumin Zhang, Weidong Zhu, Maohong Fan
Summary: The photocatalytic technology of reducing CO2 into high value-added chemicals and fuels can mitigate energy shortages and environmental problems caused by greenhouse effects. This study successfully improved the photocatalytic performance of Zr-MOF for CO2 reduction by covalent modification, demonstrating the potential of modifying MOFs to enhance the photocatalytic efficiency of CO2 reduction.
JOURNAL OF ENVIRONMENTAL SCIENCES
(2023)
Article
Chemistry, Applied
Da-Ping Jin, Shi-Qi Cao, Fu Cheng, Ze-Sen Xue, Run-Ze Li, Yan-Lin Pu, Dao-Yong Zhu, Wen Bao, Xue-Tao Xu, Shao-Hua Wang
Summary: An Au(I)-catalyzed cascade reaction involving cyclization and semipinacol rearrangement of 1,6-enynes has been developed for the synthesis of spiro[4.5]decanes and 7-azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF catalyst led to the formation of functionalizable spirocyclic products with high diastereoselectivity ranging from 6.7:1 to > 20:1 dr. A plausible reaction mechanism has been proposed based on previous literature and experimental findings.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yaping Song, Ruifang Xue, Li Wang, Nan Li, Zhijun Fang, Yanghe Fu, De-Li Chen, Weidong Zhu, Fumin Zhang
Summary: A chemoselective reductive heterocyclization route is used for direct synthesis of 2,1-benzisoxazole and related compounds. The transformation of feedstocks using hydrogen as a hydrogen source at ambient temperature and atmospheric pressure remains a challenge.
Article
Chemistry, Physical
Nan Li, Changping Jian, Yaping Song, Li Wang, Ata Ur Rehman, Yanghe Fu, Fumin Zhang, De-Li Chen, Weidong Zhu
Summary: Here, a facile and scalable approach for synthesizing Fe-based MOF MIL-88A(Fe) via a liquid-phase route at atmosphere pressure is reported. The synthesized MIL-88A(Fe) nanocrystals exhibit high crystallinity, monodispersed particle size, and large specific surface area. These nanocrystals serve as a heterogeneous catalyst for the efficient aerobic oxidation of cyclohexene to 2-cyclohexene-1-ol with high conversion (81%) and selectivity (70%). The reaction mechanism involves both free radical and Fe-mediated pathways.
MOLECULAR CATALYSIS
(2023)
Article
Engineering, Environmental
Yaping Song, Rou Guo, Binbin Feng, Yanghe Fu, Fumin Zhang, Yifei Zhang, De-Li Chen, Jiangwei Zhang, Weidong Zhu
Summary: A facile strategy to modulate the coordination number of Zn single atoms and enhance the catalytic activity for transfer hydrogenation was reported. The Zn-N3 coordination in the catalyst exhibited the best performance.
CHEMICAL ENGINEERING JOURNAL
(2023)
Review
Environmental Sciences
Ke Guo, Ijaz Hussain, Guang'an Jie, Yanghe Fu, Fumin Zhang, Weidong Zhu
Summary: This review discusses the recent breakthroughs in photocatalytic CO2 reduction, focusing on the use of metal-organic frameworks (MOFs) as new catalysts. Various techniques for modifying MOFs and integrating them with other materials have been explored and summarized. The challenges and future prospects of MOFs as photocatalysts for CO2 reduction are also discussed.
JOURNAL OF ENVIRONMENTAL SCIENCES
(2023)
Article
Energy & Fuels
Ata Ur Rehman, Tianyu Zhao, Ihsan Muhammad, Shehla Rasheed, Rahim Shah, Adnan Raza Altaf, Fumin Zhang, Sining Yun
Summary: Researchers synthesized a new MgCl2/MXene (Ti3C2Tx) composite sorbent for low-temperature thermochemical heat storage through the impregnation method. Various techniques were used to characterize the mechanical and thermal properties of the MgCl2/MXene composites. The results showed that the MXene-based composites exhibited improved adsorption properties and cyclic stability compared to pure MgCl2. The water sorption kinetics and energy storage density of the composites were also evaluated, indicating their potential for long-term heat storage applications.
JOURNAL OF ENERGY STORAGE
(2023)
Article
Chemistry, Physical
Huilin Jia, Baihui Zhu, Xiaoyan Zhi, Yuexian Du, Jiahui Liu, Guang'an Jie, Yanghe Fu, Rui Ma, Fumin Zhang, Weidong Zhu
Summary: As a new type of porous organic materials, two-dimensional covalent organic frameworks (2D COFs) show superior visible-light harvesting and effective separation and transport of the photogenerated charges, which ensures COFs to be promising platforms for photocatalysis. In this study, two 2D imine-linked COFs (PDA-TAB and PDA-TTA) were synthesized to investigate the effects of the introduced triazine units in the skeleton of COFs on photocatalytic CO2 reduction. The results showed that PDA-TTA exhibited a much higher photocatalytic activity compared to PDA-TAB, with a HCOOH yield of 65.7 mu mol g(cat)(-1)h(-1). Further studies indicated that the introduction of triazine units in the skeleton of PDA-TTA not only enhanced the visible-light absorption but also promoted the charge separation and migration, thereby improving the photocatalytic performance. This work contributes to the understanding of the roles of key structural units in 2D COFs in photocatalysis and provides insights for the development of efficient photocatalysts for CO2 conversion.
Article
Chemistry, Multidisciplinary
Jie Chen, Mingyuan Jian, Lei Zhuang, Wenting Lin, Yanghe Fu, De-Li Chen, Weidong Zhu, Guihua Chen, Fumin Zhang
Summary: A series of N-doped porous carbon-supported CeO2 and ZrO2 nanoparticle catalysts were prepared, and CeZr-NC-1073 showed outstanding catalytic activity and stability.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Ke Guo, Guang'an Jie, Jiahui Liu, Yanghe Fu, Rui Ma, Xinqing Lu, Fumin Zhang, Weidong Zhu, Maohong Fan
Summary: This study demonstrates the potential of using a metal-organic framework as a photocatalyst for the selective oxidation of amines and sulfides, resulting in the production of valuable imines or sulfoxides with high selectivity. The reactive oxygen species, including superoxide radicals and hydroxyl/peroxyl radicals, play crucial roles in the photocatalytic reactions.
SUSTAINABLE ENERGY & FUELS
(2022)
Article
Chemistry, Inorganic & Nuclear
Wu Xiao-Xue, Qi Yan-Yan, Wang Ying-Yi, Wang Li, Tu Gao-Mei, Fu Yang-He, Chen De-Li, Zhu Wei-Dong, Zhang Fu-Min
Summary: A vanadium-nitrogen co-doped porous carbon (V-N-C) catalyst was prepared via high-temperature pyrolysis and acid-leaching, and it exhibited excellent catalytic activity and selectivity in the oxidative coupling reaction of benzylamine, as well as good universality for various substrates.
CHINESE JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiaoxue Wu, Wenting Lin, Li Wang, Nan Li, Gaomei Tu, Yanghe Fu, De-Li Chen, Weidong Zhu, Guihua Chen, Fumin Zhang
Summary: In this study, highly dispersed Pd nanoclusters anchored on HfO2 support were fabricated as catalysts and showed excellent catalytic activity and stability for the Suzuki-Miyaura coupling reaction, indicating significant potential for industrial application.
NEW JOURNAL OF CHEMISTRY
(2022)