Article
Chemistry, Multidisciplinary
Shuang Liu, Zhe Zhuang, Jennifer X. Qiao, Kap-Sun Yeung, Shun Su, Emily C. Cherney, Zheming Ruan, William R. Ewing, Michael A. Poss, Jin-Quan Yu
Summary: A novel catalytic system was reported for the intramolecular gamma-C-H amination of aliphatic amides derived from amino acids, enabling the convenient synthesis of lactams, isoindolinones, and 2-imidazolidinones. This protocol demonstrates the utility of utilizing N-acyl amino acids as directing groups and cyclization partners, tert-butyl hydrogen peroxide as the sole oxidant, and a broad substrate scope for the construction of important structural cores of medicinal compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Liang Hu, Guangrong Meng, Jin-Quan Yu
Summary: This study reports the first Pd(II)-catalyzed intermolecular fi-methylene C(sp3)-H arylation of free aliphatic acids using bidentate pyridine-pyridone ligands. The bite angle of the ligand plays a key role in promoting fi-methylene C-H activation of free carboxylic acid. This transformation provides a disconnection for alkylation of arenes with simple aliphatic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yangyang Wang, Xiaobo Xu, Binghan Pang, Liqiang Hao, Gaorong Wu, Yafei Ji
Summary: In this study, the palladium-catalyzed sequential C(sp(3))-H and C(sp(2))-H bond diolefination reaction of o-toluidine was achieved using acetyl-protected aminoethyl phenyl thioether ligands. This novel reaction allows for the preparation of conjugated diene structure via an immediate second olefination, based on the first C(sp(3))-H olefination, in one pot. Various triflyl-protected anilines and acrylates were elegantly used as coupling partners. Furthermore, the unpurified diolefination products can be easily converted to tetrahydroquinoline derivatives.
Article
Multidisciplinary Sciences
Jiping Hao, Xueying Guo, Shijun He, Zhongliang Xu, Lu Chen, Zhongyu Li, Bichao Song, Jianping Zuo, Zhenyang Lin, Weibo Yang
Summary: The biomimetic assembly strategy has successfully synthesized diverse furan-embedded macrolactams with significant anti-inflammatory activities and cytotoxicity comparable to Dexamethasone. This approach avoids the use of unstable and toxic compounds, demonstrating the potential for future drug development.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Md. Emdadul Hoque, Jin-Quan Yu
Summary: In this study, we report a new method for the gamma-arylation and gamma-lactonization of aliphatic acids, enabled by a L,X-type CarboxPyridone ligand catalyzed Pd(II) reaction. A wide range of gamma-arylated gamma-lactones can be efficiently synthesized in a single step, and the arylated lactones can be further converted into disubstituted tetrahydrofurans, which are prominent scaffolds in bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xandro Vidal, Jose Luis Mascarenas, Moises Gulias
Summary: The palladium-catalyzed formal (4 + 2) cycloaddition reaction described in the study offers a direct and unconventional approach to tetrahydroquinoline skeletons through the activation of C(sp(3))-H bonds. The reactivity can also be extended to ortho-methyl benzylamides, allowing for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process.
Article
Chemistry, Organic
Canlin Zou, Hongting Wu, Jiangtao He, Yunfei Hu, Weijie Deng, Xinling Li, Jinhui Hu, Yibiao Li, Yubing Huang
Summary: An efficient anodic C(sp(3))-H acyloxylation protocol has been developed, which enables the direct oxidation of indolin-3-ones to obtain various C2-acyloxy indolin-3-ones without the need for metal catalysts and external oxidants. The practicality of this protocol has been demonstrated through the effective application of several medical drugs and gram-scale experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhen Li, Jin-Quan Yu
Summary: Selective hydroxylation of gamma-C-H bonds from abundant amine feedstocks using sustainable aqueous hydrogen peroxide has been achieved via palladium catalysis. This ligand-enabled method provides excellent monoselectivity for a range of primary amines, piperidines, and morpholines at the gamma-position, enabling the synthesis of various amines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Hui -Lin Liu, Zeng He, Na-Na Wang, Hao Xu, Ping Fang, Tian-Sheng Mei
Summary: A C(sp(3))-H alkenylation method of tetrahydroisoquinoline is developed by merging Shono oxidation and the Morita-Baylis-Hillman reaction, using 4-dimethylaminopyridine as an organocatalyst and TEMPO/NaBr as an electrocatalyst. The reaction proceeds through the interception of an iminium cation intermediate generated in situ from anodic oxidation, leading to unconventional aza-Morita-Baylis-Hillman reaction products. Additionally, the use of TEMPO and NaBr as mediators is crucial to prevent the decomposition of products by lowering the oxidation potential of the reaction.
Article
Chemistry, Organic
Hui-Lin Liu, Zeng He, Na-Na Wang, Hao Xu, Ping Fang, Tian-Sheng Mei
Summary: In this study, a C(sp3)-H alkenylation of tetrahydroisoquinoline was achieved by merging Shono oxidation and the Morita-Baylis-Hillman reaction. A 4-dimethylaminopyridine organocatalyst and TEMPO/NaBr electrocatalyst were utilized. The reaction proceeds through the interception of an iminium cation intermediate generated from anodic oxidation, leading to aza-Morita-Baylis-Hillman reaction products. The use of TEMPO and NaBr as mediators is crucial to prevent product decomposition by lowering the oxidation potential.
Article
Chemistry, Multidisciplinary
Zhe Zhuang, Shuang Liu, Jin-Tang Cheng, Kap-Sun Yeung, Jennifer X. Qiao, Nicholas A. Meanwell, Jin-Quan Yu
Summary: In this study, a novel C-H functionalization reaction was reported, which utilizes common protecting groups and practical oxidants for the lactamization of tosyl-protected aliphatic amides. The reaction was enabled by a specific ligand and shows mild reaction conditions, good scalability, and the use of convenient oxidants and protecting groups. Further derivatization of the beta-lactam products allows the synthesis of various biologically significant compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kunsoon Kim, Seulchan Lee, Soon Hyeok Hong
Summary: A highly efficient, direct C(sp(3))-H cyanation method was developed under mild photocatalytic conditions, allowing for the direct cyanation of various C(sp(3))-H substrates with excellent functional group tolerance. Complex natural products and bioactive compounds can be efficiently cyanated using this method.
Article
Chemistry, Multidisciplinary
Tao Sheng, Zhe Zhuang, Zhen Wang, Liang Hu, Alastair N. Herron, Jennifer X. Qiao, Jin-Quan Yu
Summary: The study presents a novel method for the dehydrogenation-olefination-lactonization of aliphatic acids, providing a unique approach to diversify structures. The use of newly designed bidentate ligands is crucial for the success of this tandem reaction, enabling preferential methylene C-H activation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Bijin Li, Mazen Elsaid, Haibo Ge
Summary: C(sp(3))-H functionalization is an important method to increase molecular complexity. Despite the initial challenges of inertness and high bond-dissociation energies, these hurdles can be overcome through selective strategies, leading to efficient construction of C-C and C-X bonds. This review discusses transition-metal-catalyzed site-selective gamma- and delta-C(sp(3))-H functionalization reactions and explores their applications in late-stage functionalization of medicinal compounds and construction of complex molecules of medicinal importance.
Article
Chemistry, Multidisciplinary
Qian Gao, Senmiao Xu
Summary: We report a carbamate-directed iridium-catalyzed asymmetric beta-C(sp(3))-H borylation of strained (hetero)cycloalkanes. Densely functionalized cyclopropanols were obtained in good enantioselectivities via desymmetrization and kinetic resolution. Site-selective C(sp(3))-H borylation of methine groups provided alpha-borylated (hetero)cycloalkanols in moderate to good yields. The synthetic utility of the method was demonstrated in a gram-scale synthesis and various downstream transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Jian He, Masayuki Wasa, Kelvin S. L. Chan, Ojan Shao, Jin-Quan Yu
Article
Chemistry, Multidisciplinary
Ru-Yi Zhu, Tyler G. Saint-Denis, Ying Shao, Jian He, Joshua D. Sieber, Chris H. Senanayake, Jin-Quan Yu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Jian He, Qian Shao, Qingfeng Wu, Jin-Quan Yu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Qian Shao, Qing-Feng Wu, Jian He, Jin-Quan Yu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Physical
Jian He, Caiyou Chen, Gregory C. Fu, Jonas C. Peters
Article
Chemistry, Multidisciplinary
Ji-Kang Jin, Kun Wu, Xin-Yi Liu, Guo-Quan Huang, Yong-Liang Huang, Dong Luo, Mo Xie, Yifang Zhao, Weigang Lu, Xiao-Ping Zhou, Jian He, Dan Li
Summary: Charge separation is crucial in regulating photochemical properties in photocatalysts design. Metal-organic frameworks (MOFs) are promising candidates for heterogeneous photocatalysis due to their designability and photon absorption tunability. A pyrazole-benzothiadiazole-pyrazole organic molecule with a donor-acceptor-donor conjugated pi-system was designed for fast charge separation, resulting in a more effective heterogeneous photocatalyst JNU-204, which demonstrated stability and reusability in aerobic oxidation reactions under visible-light irradiation. JNU-204 also showed applications in the synthesis of marine natural product core skeletons.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Xia Wu, Xiao Xiong, Jia-Li Li, Dong Luo, Kun Wu, Yu-Bai Wei, Xin-Yi Liu, Weigang Lu, Dan Li, Jian He
Summary: Due to misuse and poor management, antibiotics pose a significant threat to the ecological environment and human health. Developing highly sensitive and effective sensors to detect environmental contaminants is a crucial and challenging task. Biological metal-organic frameworks, as a new class of desirable biocompatible materials, show promise as a viable platform for sensing applications.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ben Ma, Qi Xia, Deyang Wang, Ji-Kang Jin, Zekun Li, Qiu-Jiang Liang, Meng-Ying Sun, Dongyi Liu, Li-Juan Liu, Hui-Xing Shu, Jun Yang, Dan Li, Jian He
Summary: Visible-light copper photocatalysis has become a viable technology for sustainable synthetic processes. In this study, a metal-organic framework (MOF)-supported copper(I) photocatalyst was developed for iminyl radical-mediated reactions. The heterogenized copper photosensitizer exhibited higher catalytic activity than its homogeneous counterpart due to site isolation. The immobilization of copper species on MOF supports using a hydroxamic acid linker allowed for high recyclability of the heterogeneous catalysts and the preparation of previously unavailable monomeric copper species through post-synthetic modification on MOF surfaces. This study highlights the potential of MOF-based heterogeneous catalytic systems in addressing challenges in synthetic methodologies and mechanistic investigations of transition-metal photoredox catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shengli Zhuang, Dong Chen, Wai-Pan Ng, Li-Juan Liu, Meng-Ying Sun, Dongyi Liu, Tehseen Nawaz, Qi Xia, Xia Wu, Yong-Liang Huang, Seungkyu Lee, Jun Yang, Jun Yang, Jian He
Summary: By substituting neutral phosphine ligands for surface anionic thiolate ligands, two atomically precise defective Au-44 nanoclusters were successfully formed. The Au-44(PPh3)(TBBT)(26) nanocluster with major structural defects showed superior electrocatalytic performance in the CO2 reduction to CO, which was attributed to the active site near the defects.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Li-Juan Liu, Fahri Alkan, Shengli Zhuang, Dongyi Liu, Tehseen Nawaz, Jun Guo, Xiaozhou Luo, Jian He
Summary: This study reports a new type of gold nanoclusters, whose intrinsic chirality arises solely from the arrangement of the organic components on their surface. The highly dynamic behaviors of aromatic rings in the thiolates assembled via pi - pi stacking and C - H center dot center dot center dot pi interactions explain the non-asymmetrically induced inner structures of these nanoclusters. This work introduces an important class of nanoclusters with intrinsic chirality from surface layers and helps elucidate the transition of gold nanoclusters from their molecular to metallic states.
NATURE COMMUNICATIONS
(2023)
Article
Engineering, Environmental
Tehseen Nawaz, Muhammad Ahmad, Mohd Zahid Ansari, Iftikhar Hussain, Xi Chen, Li-Juan Liu, Rajat Walia, Kam Hung Low, Shengli Zhuang, Kaili Zhang, Jian He
Summary: Fast-charging storage devices have gained attention for their potential applications in microelectronic gadgets and hybrid electric vehicles. The use of atomically precise metal nanoclusters (NCs) in supercapacitors is rare, but the synthesis of structurally distorted doped Au38_xAgx NCs protected by 2,4-dimethylbenzenethiolate (2,4-DMBT) and their integration with ZIF-8 (Au38_xAgx NCs@ZIF-8) have been studied for electrochemical and physicochemical research. The enhanced electronic transfer kinetics and improved specific capacitance make the doped Au38_xAgx NCs@ZIF-8 based hybrid supercapacitor (HSC) a promising option for next-generation energy storage devices.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Shengli Zhuang, Dong Chen, Wai-Pan Ng, Dongyi Liu, Meng-Ying Sun, Xia Wu, Yao Zhang, Zekun Li, Yong-Liang Huang, Jun Yang, Jun Yang, Jian He
Summary: This study successfully synthesized a phosphinous acid-phosphinito gold nanocluster with a tetra-icosahedral kernel using a mixed-ligand strategy, and found that phosphinous acid-phosphinito ligands exhibit excellent catalytic activity in electrocatalytic reactions.
Article
Chemistry, Multidisciplinary
Shengli Zhuang, Dong Chen, Wai-Pan Ng, Dongyi Liu, Li-Juan Liu, Meng-Ying Sun, Tehseen Nawaz, Xia Wu, Yao Zhang, Zekun Li, Yong-Liang Huang, Jun Yang, Jun Yang, Jian He
Summary: In this study, a gold nanocluster with a tetra-icosahedral kernel was successfully synthesized using a mixed-ligand strategy. It was found to exhibit high stability and excellent electrocatalytic performance in the oxygen reduction reaction.
Article
Chemistry, Multidisciplinary
Huai-Wei Wang, Yi Lu, Bing Zhang, Jian He, Hua-Jin Xu, Yan-Shang Kang, Wei-Yin Sun, Jin-Quan Yu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Haiyan Fu, Peng-Xiang Shen, Jian He, Fanglin Zhang, Suhua Li, Peng Wang, Tao Liu, Jin-Quan Yu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
