Article
Chemistry, Multidisciplinary
Carmela De Risi, Arianna Brandolese, Graziano Di Carmine, Daniele Ragno, Alessandro Massi, Olga Bortolini
Summary: Oxidative N-heterocyclic carbene (NHC) catalysis has the potential to achieve oxidative and oxygenative transformations, generating various NHC-bound intermediates and enabling non-umpolung processes through the activation of carbon atoms and heteroatoms. This review aims to discuss the recent developments in the field of oxidative NHC catalysis since 2014, with a focus on pivotal intermediates and their mechanistic involvement. More details can be found in the review article by C. De Risi and co-workers.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Carmela De Risi, Arianna Brandolese, Graziano Di Carmine, Daniele Ragno, Alessandro Massi, Olga Bortolini
Summary: Oxidative N-heterocyclic carbene (NHC) catalysis enables oxidative and oxygenative transformations, producing various NHC-bound intermediates and facilitating non-umpolung processes by activating carbon atoms and heteroatoms. This review discusses the developments in the literature on oxidative NHC catalysis since 2014, with a specific focus on pivotal intermediates and their mechanistic involvement.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Simon Stenkvist, Sara Bacaicoa, Ellymay Goossens, Henrik Sunden
Summary: The use of oxidative N-heterocyclic carbene (NHC) catalysis has gained significant interest due to the ease of transforming simple starting materials into highly functionalized products. However, the use of stoichiometric amounts of high molecular weight oxidants usually generates equivalent amounts of waste. To address this issue, the use of oxygen as the terminal oxidant in NHC catalysis has been developed. This review covers the development of aerobic oxidative carbene catalysis, including NHC-catalyzed reactions with oxygen, strategies for oxygen activation, and selectivity issues under aerobic conditions.
Article
Chemistry, Multidisciplinary
Wacharee Harnying, Panyapon Sudkaow, Animesh Biswas, Albrecht Berkessel
Summary: Simple carboxylic acids, like benzoic acid, have been found to enhance the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A protocol using a novel N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt as catalyst and benzoic acid as co-catalyst was developed for the transformation of a wide range of sterically hindered alpha- and beta-substituted aliphatic aldehydes/enals. The observed effect is believed to be due to the carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tingting Li, Chengli Mou, Puying Qi, Xiaolin Peng, Shichun Jiang, Gefei Hao, Wei Xue, Song Yang, Lin Hao, Yonggui Robin Chi, Zhichao Jin
Summary: A catalytic atroposelective cycloaddition reaction between thioureas and ynals has been developed, enabling the establishment of C-N axial chirality with excellent optical purities. The resulting axially chiral thiazine derivative products contain multiple functional groups and are suitable for further transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hui Tan, Shen-An Wang, Zixi Yan, Jianzhong Liu, Jialiang Wei, Song Song, Ning Jiao
Summary: This study demonstrates a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of organic halides into esters utilizing O-2 as the oxygen source. Mechanistic studies show the oxidation of deoxy Breslow intermediate to Breslow intermediate for further transformation. This method expands the field of NHC catalysis and promotes oxygenation reactions with O-2.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Ruonan Chen, Hongyan Yuan, Yawen Wang, Hongyu Chen, Yanhua Zhang
Summary: This study reports the electrochemical decarboxylation for Csp3-N coupling between aliphatic carboxylic acids and N heterocycles. Various Nalkylation products are obtained in moderate to good yields using CF3SO2Na under ambient conditions in CH3CN with constant current. The use of Co(OAc)2 · 4H2O catalyst enables satisfying functional-group tolerance for both primary and secondary carboxylic acids, which has not been achieved in previous works.
Article
Chemistry, Multidisciplinary
Qiuming Liang, Kasumi Hayashi, Longfei Li, Datong Song
Summary: The dioxygenation of mesoionic N-heterocyclic olefins (mNHOs) using molecular dioxygen has been reported. Depending on the presence of a vinyl proton and acidic C-H group, the mNHOs are oxidized into different products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ekaterina S. Sheina, Tatyana S. Shestakova, Sergey L. Deev, Igor A. Khalymbadzha, Pavel A. Slepukhin, Oleg S. Eltsov, Alexander S. Novikov, Vadim A. Shevyrin, Valery N. Charushin, Oleg N. Chupakhin
Summary: The C-N coupling of 1,2,4-triazolo[1,5-a]pyrimidin-7-ones with 1-adamantanol/1-bromoadamantane leads to the formation of 1,2,4-triazolo[4,3-a]pyrimidinium-5-olates, which are mesomeric betaines (MBs). The structures of the products were confirmed using X-ray analysis and 1D C-13 NMR spectra. Treatment of the betaines with LiHMDS resulted in the formation of anionic carbenes, which were detected using C-13 NMR spectroscopy.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Arne Merschel, Dennis Rottschaefer, Beate Neumann, Hans-Georg Stammler, Mark Ringenberg, Maurice Van Gastel, T. Ilgin Demirer, Diego M. M. Andrada, Rajendra S. S. Ghadwal
Summary: In this study, we have successfully synthesized and isolated two stable anions K[SIPrBp] (4 a-K) and K[IPrBp] (4 b-K). These anions, derived from classical N-heterocyclic carbenes (NHCs), exist as violet crystalline solids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Moloud Mokfi, Joerg Rust, Christian W. Lehmann, Fabian Mohr
Summary: Xanthine derivatives can be readily ethylated at N9 using cheap alkylating agents to form various silver(I) carbene complexes. These complexes play important roles in transmetallation reactions with transition metal elements, and can be characterized by various spectroscopic methods and X-ray diffraction.
Article
Chemistry, Multidisciplinary
Bastiaan Kooij, Zhaowen Dong, Paul Varava, Farzaneh Fadaei-Tirani, Rosario Scopelliti, Laura Piveteau, Kay Severin
Summary: This study reports the preparation and structural characterization of vanadium complexes with N-heterocyclic vinylidene ligands, enabled by utilizing diazoolefins as ligand precursors. Structural and theoretical analysis show that N-heterocyclic vinylidenes can act as strong 6e(-) donor ligands, forming strong metal-carbon interactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Runxia Nan, Yiwen Li, Zhouli Zhu, Fan Qi, Xu-Qiong Xiao
Summary: This study focused on the synthesis and transformation of functional groups in metallacarboranes, and investigated their impact on the structure and properties of the metallacarborane framework.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Iris Berg, Einav Amit, Lillian Hale, F. Dean Toste, Elad Gross
Summary: In this study, a N-heterocyclic carbene (NHC) nanolayer was successfully anchored on the surface of a copper electrode using an electrochemical method, resulting in improved oxidation resistance of copper.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
K. E. Shepelenko, S. B. Soliev, K. A. Nikolaeva, M. E. Minyaev, V. M. Chernyshev
Summary: An efficient catalytic system based on commercially available nickel source, N-heterocyclic carbene, and a reducing agent was developed for the selective C(5)H-alkylation of amides and esters of 2-furancarboxylic acid with alkenes of various structures. A series of previously undescribed 5-alkyl derivatives of 2-furancarboxylic acid were successfully synthesized.
RUSSIAN CHEMICAL BULLETIN
(2023)
Article
Clinical Neurology
Yuwen Cao, Jingying Wu, Yunhua Yue, Chao Zhang, Shihua Liu, Ping Zhong, Shige Wang, Xiaojun Huang, Weiping Deng, Jing Pan, Lan Zheng, Qing Liu, Liang Shang, Benyan Zhang, Jie Yang, Guang Chen, Shufen Chen, Li Cao, Xinghua Luan
Summary: NIID is a heterogeneous neurodegenerative disease with multiple clinical subtypes. The clinical features of Chinese NIID patients include variable onset age and disease duration, with common phenotypes such as tremor, dementia, and paroxysmal encephalopathy. Pathological examinations combined with genetic testing are the gold standard for diagnosis, and the involvement of lysosomal and mitochondrial dysfunction in the pathogenesis of NIID warrants further study.
ACTA NEUROLOGICA BELGICA
(2022)
Article
Chemistry, Multidisciplinary
Jian Zhang, Wu-Lin Yang, Hanliang Zheng, Yi Wang, Wei-Ping Deng
Summary: This study reports an unprecedented asymmetric gamma-allylic alkylation method using the Sc/Ir dual catalysis system, which provides synthetically versatile gamma-allylic crotonaldehydes with high efficiency and excellent selectivities. The dienolates, without essential auxiliary groups, are generated in situ through scandium triflate-mediated Meinwald rearrangement in an atom-economical manner. A Sc/Ir bimetallic catalytic cycle is proposed to explain the reaction mechanism using computational density functional theory calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wu-Lin Yang, Xin-Yu Shang, Xiaoyan Luo, Wei-Ping Deng
Summary: The enantioselective cascade reaction between racemic 2-(1-hydroxyallyl)phenols and alkynols/alkynamides was achieved using a gold and iridium sequential catalytic system. This method provides efficient access to spiroketals and spiroaminals with excellent enantioselectivities. The synthetic utility of this method has been demonstrated by the enantioselective synthesis of an analogue of Paecilospirone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Tian Tan, Wei Wang, Kai Zhang, Zixiang Zhan, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: Plastics play important roles in modern society, but their landfilling and discarding as waste contribute to environmental pollution and carbon loss, posing high risks to ecosystems and human health. Current physical recycling methods are limited to thermoplastic recycling and suffer from quality deterioration. Catalytic upcycling has emerged as a promising strategy to treat plastic waste by upgrading it into value-added products under mild conditions. This review highlights recent advances in the development of efficient heterogeneous catalysts and useful strategies for upcycling plastics into various valuable chemicals and materials.
Article
Chemistry, Organic
Fu-Sheng He, Ping Bao, Zhimei Tang, Feiyan Yu, Wei-Ping Deng, Jie Wu
Summary: This research developed a new photoredox-catalyzed reaction method, which can introduce various functionalized sulfonyl groups into ketones through the synthesis of easily accessible starting materials and good functional group compatibility. In addition, it is the first time that α-methylsulfonated ketones have been synthesized using methanol as the methyl source, which is an important industrial raw material.
Article
Clinical Neurology
Yang Gao, Weiping Deng, Jialan Sun, Dongqi Yue, Bei Zhang, Yulan Feng, Jun Han, Fanxia Shen, Jin Hu, Yi Fu
Summary: This study aimed to explore the association of dipping patterns and other factors with lacunes and enlarged perivascular spaces (EPVS) in patients with hypertension. The results showed that nocturnal blood pressure decline was negatively correlated with lacunes and EPVS, while mean systolic blood pressure level was positively correlated with them.
FRONTIERS IN NEUROLOGY
(2022)
Article
Chemistry, Multidisciplinary
Wu-Lin Yang, Xin-Yu Shang, Tao Ni, Hui Yan, Xiaoyan Luo, Hanliang Zheng, Zhong Li, Wei-Ping Deng
Summary: In this study, an efficient iridium/silver/acid ternary catalytic system was developed for the synthesis of bisbenzannulated [6,6]-spiroketals and [6,6]-spiroaminals with high diastereo- and enantioselectivities. The reaction mechanism and stereochemistry were elucidated through experimental studies and theoretical calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Daming Zeng, Yinhao Ma, Wei-Ping Deng, Ming Wang, Xuefeng Jiang
Summary: Sulfur(VI) fluoride cleavage and exchanging linkage, a new generation of linkage chemistry, has great potential in combining functional molecules in various fields. A metal-free linkage of unactivated alkenes and sulfonimidoyl fluorides via hydrosulfonimidoylation method was established, which can efficiently construct sulfoximines. The key step in this process is an intermolecular hydride transfer process. The successful application of this linkage reaction to natural products and pharmaceuticals provides the basis for drug discovery and drug conjugation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Jun Feng, Sha Xu, Hao Du, Qiaobin Gong, Shunji Xie, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: This paper discusses the recent advances in the photocatalytic conversion of methanol into high-value chemicals, highlighting the differences between photocatalysis and thermocatalysis, as well as the key factors influencing catalytic performance. The challenges and opportunities of methanol conversion are also explored.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Applied
Kai Zhang, ZiXiang Zhan, Minzhi Zhu, Haiwei Lai, Xiangyang He, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: This article introduces an efficient electrocatalytic system using nickel oxide (NiO) and TEMPO or ACT as catalysts, which selectively oxidize key bio-platform molecules such as glucose, xylose, and 5-hydroxymethylfurfural (HMF) into corresponding dicarboxylic acids. NiO catalyzes the oxidation of aldehyde to carboxylic acid, while TEMPO or ACT oxidizes primary alcohol to aldehyde. The combination of NiO and TEMPO or ACT significantly accelerates the tandem oxidation of aldehyde and hydroxyl groups, achieving excellent yields (83%-99%) of dicarboxylic acids. Moreover, the combination catalyst enables the selective oxidation of glucose and xylose with high concentrations, offering a promising strategy for biomass valorization.
JOURNAL OF ENERGY CHEMISTRY
(2023)
Editorial Material
Chemistry, Applied
Weiping Deng, Ye Wang
JOURNAL OF ENERGY CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenqi Liu, Meng Zang, Jian Zhang, Quannan Wang, Yang-Zi Liu, Wei-Ping Deng
Summary: An efficient method for the construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed. This reaction demonstrates a high tolerance towards various functional groups and shows exclusive regioselectivity, resulting in a series of nine-membered heterocycles in moderate to excellent yields. The synthetic utility of the method has been further demonstrated by a gram-scale reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Tao Ye, Fangyuan Cheng, Jian Zhang, Yang-Zi Liu, Quannan Wang, Wei-Ping Deng
Summary: In this paper, a palladium-catalyzed C-H carbonylation reaction of gem-disubstituted ethylenes with phenyl formate as a convenient CO surrogate is reported. The reaction proceeds through an aryl to vinyl 1,4-palladium migration, providing a wide range of beta, beta-diaryl substituted alpha, beta-unsaturated esters with high efficiency and excellent regio- and stereoselectivities. The synthetic protocol presented in this study offers a convenient and powerful method to directly access a key intermediate for (Z)-tamoxifen.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Zhang Jian, Chen Ying, Wang Quannan, Shen Jiahuan, Liu Yangzi, Deng Weiping
Summary: The article introduces the asymmetric synthesis of chiral heterocyclic compounds using transition metal-catalyzed cyclization, focusing on the application and issues of allyl or propargyl heteroatom-dipole precursors.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wu-Lin Yang, Jia-Huan Shen, Zeng-Hui Zhao, Zhongao Wang, Wei-Ping Deng
Summary: In this study, a gold/palladium bimetallic relay catalytic strategy was developed for the synthesis of furan-fused azepines with excellent enantioselectivities. Enynamides were activated by a gold catalyst to generate azadienes in situ, which then reacted with Pd-TMM via the asymmetric [4 + 3] cycloaddition process. Furthermore, oxidative furan cleavage of the cycloadducts mediated by potassium nitrate allowed the synthesis of poly-functionalized enantioenriched azepines under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.