Article
Chemistry, Multidisciplinary
Xuetong Li, Jordi Benet-Buchholz, Eduardo C. Escudero-Adan, Arjan W. Kleij
Summary: A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. The chemoselectivity is achieved through a proper design of the precursor and the use of Thorpe-Ingold effects. The synthetic diversity of these CO2-based heterocycles is demonstrated, and an unusual ring-expansion sequence is observed from an alpha-alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Shuai Wang, Xin Li, Shengnan Jin, Kang Liu, Cong Dong, Jianke Su, Qiuling Song
Summary: In this study, an efficient and general synthesis method for constructing 1,3-oxazin-6-ones was reported. The method features high efficiency and chemoselectivity, using difluorocarbene as a carbonyl provider. It offers readily available starting materials, valuable products, good functional group tolerance, and simple operation.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Anastasiya Agafonova, Pavel A. Sakharov, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A fundamentally new radical cascade reaction of 2-acyloxyazirines provides a one-step method for the preparation of 5-hydroxy-6H-1,3-oxazin-6-ones. The reaction can be applied to various 2-acyloxy-substituted methyl azirine-2-carboxylates, with the volume of the acyloxy substituent influencing the formation of a side product. Additionally, the hydroxyl group in the resulting product can be easily replaced with different groups through palladium-catalyzed cross-coupling reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Chuan-Kun Ran, Lei Song, Ya-Nan Niu, Ming-Kai Wei, Zhen Zhang, Xiao-Yu Zhou, Da-Gang Yu
Summary: This study demonstrates the simultaneous utilization of elemental sulfur and CO2 in a multi-component reaction to generate valuable products efficiently. The transition-metal-free reaction conditions allow for the conversion of readily available arylamines to thiazolidin-2-ones and 1,3-thiazinan-2-ones through C-H bond functionalization, showcasing high step economy and good functional groups tolerance.
Article
Chemistry, Organic
Yanan Liu, Pui Ying Choy, Demao Wang, Mengdi Wu, Qiang Tang, Xinwei He, Yongjia Shang, Fuk Yee Kwong
Summary: A 1,8-diazabicyclo[5.4.0]-undec-7-ene-promoted cascade double-annulation of ortho-alkynyl quinone methide is developed for constructing of 2-aryl-4-hydroxybenzo-[c]-chromen-6-ones. This method offers operational simplicity and good functional group compatibility.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jiahui Duan, Xinwei He, Pui Ying Choy, Qi Wang, Mengqing Xie, Ruxue Li, Keke Xu, Yongjia Shang, Fuk Yee Kwong
Summary: The study achieved a functionalized benzo[c]chromen-6-one core through a DBU-mediated cascade strategy, involving a sequence of reactions including 1,4-conjugate addition, lactonization, alkyne-allene isomerization, enol-keto tautomerization, 6p-electrocyclization, and aromatization. The resulting products exhibit fluorescence properties, showing potential for fluorescent material applications.
Article
Chemistry, Organic
Jing Tao, Ting-Ting Yang, Qing-Hua Li, Tang-Lin Liu
Summary: A novel transition-metal-free cyano 1,3-migration method for synthesizing β-cyano ketones with high yields, broad substrate scope, and good functional group tolerance is reported. Mechanistic study shows DBU plays multiple roles in this system.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Minghui Qi, Muhammad Suleman, Jiale Fan, Ping Lu, Yanguang Wang
Summary: Here, a copper(I)-catalyzed ring expansion reaction of isoxazoles with 4-diazoisoquinolin-3ones is reported, providing a series of densely substituted novel spiro[isoquinoline-4,2'-[1,3]oxazin]-3-ones in good to excellent yields. The prominent features of this methodology include broad substrate scope, readily available starting materials, cheap catalyst, mild reaction conditions, and scalability.
Article
Chemistry, Organic
Sengodagounder Muthusamy, Muthukumar Malarvizhi, Eringathodi Suresh
Summary: The study presents an unambiguous and precise method for the synthesis of 3,1-benzoxathiin-4-ones/1,3-benzodioxin-4-ones using propargylic alcohols and salicylic/thiosalicylic acids under catalyst-free and open-air conditions. This strategy is shown to be quite general, yielding benzoxathiinones/benzodioxinones in good amounts with various 2-mercapto and 2-hydroxybenzoic acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Yi-Ming Zhu, Wan Zhang, Hongkun Li, Xiao-Ping Xu, Shun-Jun Ji
Summary: A novel palladium-catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed, involving a cascade process of ring-opening/cyclization. The reaction shows high atomic economy with no elimination of CO2, and the obtained products exhibit aggregation-induced emission properties with relatively high solid-state emission efficiencies.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Zhenjie Qi, Simiaomiao Wen, Zhao Liu, Dongfang Jiang
Summary: A synthetic strategy to pyridazin-4(1H)-ones/oxazin-4(1H)-ones has been developed through an oxidative 6-endo-trig cyclization and [2+2] cycloaddition of β,γ-unsaturated hydrazones/ketoximes and diazonium tetrafluoroborates under metal-free conditions. This method demonstrates excellent functional group tolerance and remarkable regioselectivity. Mechanistic studies using O-18 and H-2O-18 labeling confirm the involvement of O-2 as both a reaction component and an oxidant.
Article
Biochemistry & Molecular Biology
Ehtesham U. R. Mohammed, Zoe J. Porter, Ian G. Jennings, Jasim M. A. Al-Rawi, Philip E. Thompson, Michael J. Angove
Summary: A novel series of TGX-221 analogues were synthesized by replacing the 4H-pyrido[1,2-a] pyrimidin-4-one scaffold with a 4H-benzo[e][1,3]oxazin-4-one scaffold. The analogues with an -CH(CH3) NH- linker demonstrated comparable activity to TGX-221 analogues, supported by comparative structure-activity relationship analysis. The analogues containing an -CH(CH3)O- linker exhibited lower activity but still displayed useful structure-activity relationship, including a preferred o-methyl substitution.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Physical
Wenhao Tang, Boya Li, Kewei Teng, Xiaodong Wang, Ruiping Liu, Mengwei Wu, Lei Zhang, Pengfei Ren, Junqing Zhang, Ming Feng
Summary: This review focuses on the sluggish reaction kinetics at the oxygen cathode in metal-air batteries, which is a major obstacle to their commercialization. The use of noble-metal electrocatalysts has been a potential solution, but their high cost and scarcity hinder their widespread application. The review discusses the mechanisms of oxygen reduction reaction (ORR) and oxygen evolution reaction (OER), proposes principles for bifunctional electrocatalysts, and presents state-of-the-art catalysts based on carbon and transition-metal materials. Additionally, it explores self-supporting 3D noble-metal-free bifunctional ORR/OER catalysts and provides perspectives on the future development of bifunctional electrocatalysts.
JOURNAL OF MATERIOMICS
(2022)
Article
Chemistry, Organic
Si-Jia Yu, Jie Li, Jian-Liang Ye, Pei-Qiang Huang
Summary: A one-pot reaction using palladium catalyst has been developed for the synthesis of bicyclic 1,3-oxazin-4-ones, 2,3,6,7-tetrahydrocyclopenta[e]-1,3-oxazin-4-ones and 2,3,5,6,7,8-hexahydro-4H-benzo[e]-1,3-oxazin-4-ones. The reaction shows good yields, broad substrate scope, mild reaction conditions, and scalability. It also demonstrates good compatibility with acetyl chloride and phenylacetyl chloride for the synthesis of monocyclic 1,3-oxazin-4-ones.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Chunhua Ma, Hui Meng, Jing Li, Xianguang Yang, Yuqin Jiang, Bing Yu
Summary: A comprehensive study on a transition-metal-free visible-light-promoted 3-acetalation reaction of quinoxaline-2(1H)-ones is presented. The reaction successfully constructs various acetalated quinoxaline-2(1H)-ones in moderate to good yields using an inexpensive photocatalyst and a radical source. The method demonstrates versatility in late-stage modification of drug molecules and various functionality transformations.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Jian-Heng Ye, Tao Ju, He Huang, Li-Li Liao, Da-Gang Yu
Summary: Carbon dioxide is a valuable carbon resource in organic synthesis, but its utilization is challenging due to stability and inertness. Researchers have developed radical-type carboxylations and cyclizations using visible-light photoredox catalysis and copper catalysis. These strategies have expanded the scope of CO2 transformations and provided new methods for selective organic synthesis.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Jian-Heng Ye, Peter Bellotti, Tiffany O. Paulisch, Constantin G. Daniliuc, Frank Glorius
Summary: The synthesis of beta-lactams from alpha-ketoacylsilanes and imines via a [2+2] photochemical cycloaddition enables atom-economic reactions with broad substrate scope, good functional-group tolerance, and ease of scalability. The method involves a 1,3 silicon shift to the distal carbonyl group, as suggested by experimental and computational studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jian-Heng Ye, Peter Bellotti, Corinna Heusel, Frank Glorius
Summary: A new catalytic approach for the selective functionalization of strong C-F bonds in polyfluorinated aliphatic esters and amides has been reported, allowing access to important partially fluorinated motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Yu Zhou, Xiang-Yu Li, Zhen Zhang, Da-Gang Yu
Summary: A facile synthesis of valuable pyrido[1,2-a]pyrimidine-4-thiones is reported through novel thiocarbonylation of C(sp(3))-H bonds with carbon disulfide (CS2). This reaction offers easy availability of substrates, good functional group tolerance, high yields, easy scalability, and atom economy. Mechanistic investigations suggest involvement of sulfate anion and sulfuric anhydride anion in the reaction.
CHINESE CHEMICAL LETTERS
(2021)
Article
Multidisciplinary Sciences
Guo-Quan Sun, Wei Zhang, Li-Li Liao, Li Li, Zi-Hao Nie, Jin-Gui Wu, Zhen Zhang, Da-Gang Yu
Summary: In this study, the authors successfully transformed unactivated aryl and alkyl (pseudo)halides into carboxylic acids using nickel catalysis and electricity, with atmospheric CO2 as the carbon source. This sustainable and economic strategy features mild conditions, inexpensive catalyst, and a broad substrate scope, avoiding the use of sacrificial electrodes. The reaction mechanism involves oxidative addition of aryl halides to Ni(0) complex, reduction of aryl-Ni(II) adduct to Ni(I) species, and carboxylation with CO2.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Chuan-Kun Ran, Li-Li Liao, Tian-Yu Gao, Yong-Yuan Gui, Da-Gang Yu
Summary: Carbon dioxide (CO2) is widely used as an ideal C1 source in organic synthesis due to its abundance, low cost, nontoxicity, and renewability. Recent developments in carboxylation using CO2 via transition metal catalysis, photoredox catalysis, and electrochemistry have shown significant progress, with a focus on the past two years.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2021)
Article
Cell Biology
Zhaodong Han, Rujun Mo, Shanghua Cai, Yuanfa Feng, Zhenfeng Tang, Jianheng Ye, Ren Liu, Zhiduan Cai, Xuejin Zhu, Yulin Deng, Zhihao Zou, Yongding Wu, Zhouda Cai, Yuxiang Liang, Weide Zhong
Summary: This study investigated the expression patterns and prognostic value of E2F transcription factors in patients with prostate cancer. The results showed that E2F1-3, E2F5, and E2F6 were highly expressed in prostate cancer tissues and were associated with higher Gleason score, advanced tumor stage, and metastasis. High transcription levels of E2F1-3, E2F5, E2F6, and E2F8 were also associated with a higher risk of biochemical recurrence. A prognostic model combining E2F1, E2F6, Gleason score, and clinical stage was developed to predict biochemically recurrence-free survival.
FRONTIERS IN CELL AND DEVELOPMENTAL BIOLOGY
(2022)
Article
Andrology
Zhaodong Han, Yuanfa Feng, Yulin Deng, Zhenfeng Tang, Shanghua Cai, Yangjia Zhuo, Yingke Liang, Jianheng Ye, Zhouda Cai, Shuai Yang, Yuxiang Liang, Chi Tin Hon, Jiahong Chen, Weide Zhong
Summary: The study indicates that AMIGO2 plays a critical role in numerous cancers, especially in prostate cancer (PCa). Lower expression of AMIGO2 inhibits PCa cell proliferation and colony formation. AMIGO2 serves as a reliable prognostic marker that can supplement the current prognosis evaluation system. AMIGO2 may promote PCa progression through inducing epithelial mesenchymal transition (EMT) and mediating docetaxel resistance.
TRANSLATIONAL ANDROLOGY AND UROLOGY
(2022)
Article
Chemistry, Multidisciplinary
Lin Chen, Quan Qu, Chuan-Kun Ran, Wei Wang, Wei Zhang, Yi He, Li-Li Liao, Jian-Heng Ye, Da-Gang Yu
Summary: We report a novel visible-light photocatalytic carboxylation of C-N bonds in cyclic amines with CO2 via consecutive photo-induced electron transfer (ConPET). It is the first photocatalytic reductive ring-opening reaction of azetidines, pyrrolidines, and piperidines. This strategy enables the transformation of easily available cyclic amines into valuable amino acids in moderate-to-excellent yields. The method features mild and transition-metal-free conditions, high selectivity, good functional-group tolerance, facile scalability, and product derivations. Mechanistic studies suggest that ConPET plays a key role in generating highly reactive photocatalysts for the reductive activation of cyclic amines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Immunology
Yulin Deng, Kai Guo, Zhenfeng Tang, Yuanfa Feng, Shanghua Cai, Jianheng Ye, Yuanxue Xi, Jinchuang Li, Ren Liu, Chao Cai, Zeheng Tan, Yixun Zhang, Zhaodong Han, Guohua Zeng, Weide Zhong
Summary: In this study, we established a prognostic model for ccRCC using TIL-related lncRNAs. These lncRNAs were associated with T-cell activities and may serve as biomarkers of disease prognosis.
FRONTIERS IN IMMUNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Wei Zhang, Li-Li Liao, Li Li, Yi Liu, Long-Fei Dai, Guo-Quan Sun, Chuan-Kun Ran, Jian-Heng Ye, Yu Lan, Da-Gang Yu
Summary: The dicarboxylation of unactivated skipped dienes with CO2 via electrochemistry is reported for the first time, providing valuable dicarboxylic acids. Control experiments and DFT calculations confirm the single electron transfer reduction of CO2 to its radical anion, followed by sluggish radical addition to unactivated alkenes, SET reduction of unstabilized alkyl radicals to carbanions, and nucleophilic attack on CO2 to give the desired products. This reaction possesses mild reaction conditions, broad substrate scope, facile derivations of products, and promising application in polymer chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Meng Miao, Lei Zhu, Hong Zhao, Lei Song, Si-Shun Yan, Li-Li Liao, Jian-Heng Ye, Yu Lan, Da-Gang Yu
Summary: Difunctionalizing carboxylation of alkynes with CO2 is a sustainable and important strategy to generate valuable acrylate derivatives from readily available starting materials. This study introduces a visible-light-driven and transition metal-free thio-carboxylation of alkynes with thiophenols and CO2. The use of single-electron activation of CO2 leads to unique beta-carboxylation, followed by efficient cyclizing acylation to obtain important thiochromones. The one-pot method features mild reaction conditions, high selectivity, scalability, and facile derivatization of products to bioactive compounds.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Endocrinology & Metabolism
Yuanfa Feng, Yulin Deng, Zhenfeng Tang, Shanghua Cai, Jinchuang Li, Ren Liu, Jiaming Wan, Huichan He, Guohua Zeng, Jianheng Ye, Zhaodong Han, Weide Zhong
Summary: This study identified 53 candidate markers associated with enzalutamide stimulation in prostate cancer (PCa) through single-cell RNA sequencing. Further analysis narrowed down these candidates to a 10-gene prognostic model (ENZ-sig) that can predict relapse-free survival in PCa. The effectiveness of ENZ-sig was validated in multiple independent datasets.
FRONTIERS IN ENDOCRINOLOGY
(2023)
Article
Chemistry, Physical
Jun-Ping Yue, Jin-Cheng Xu, Hai-Tian Luo, Xiao-Wang Chen, He-Xin Song, Yu Deng, Lihua Yuan, Jian-Heng Ye, Da-Gang Yu
Summary: This study reports a synergistic strategy that combines photocatalysis and copper catalysis to achieve the aminocarboxylation of alkenes with CO2, providing an efficient and practical method for the synthesis of valuable beta-amino acids. The strategy features high efficiency, mild conditions, good selectivity, strong functional group tolerance, easy product derivations, and generality in hydroamination of alkenes.
Review
Chemistry, Multidisciplinary
Li-Li Liao, Lei Song, Si-Shun Yan, Jian-Heng Ye, Da-Gang Yu
Summary: Reductive organic transformations are important in generating valuable chemicals, and visible-light photocatalysis has emerged as an ideal approach to activate inert substrates under mild conditions. This review highlights recent contributions in this field, including different excitation systems, mechanisms, and structural features, as well as limitations and potential applications.
TRENDS IN CHEMISTRY
(2022)
