Article
Chemistry, Multidisciplinary
Bo Li, Cheng-Wei Ju, Wenlong Wang, Yanwei Gu, Shuai Chen, Yongrui Luo, Haozhe Zhang, Juan Yang, Hai-wei Liang, Mischa Bonn, Klaus Mu''llen, William A. Goddard, Yazhou Zhou
Summary: The study reports a heterogeneous single-atom Pt-catalyzed Heck reaction, the first of its kind on SACs, using a supercritical carbon-dioxide-assisted protocol. The research showcases how SACs can introduce underexplored coordination structures, offering potential for transferring migratory-insertion-based reactions to heterogeneous SACs.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Chang-Rui Nie, Hong-Ping Zhao, Wang-Fu Liang, Xin-Xian Zhong, Cui Liang, Gui-Fa Su, Dong-Liang Mo
Summary: A new method for the efficient synthesis of a variety of pentacyclic chromeno[4,3-b]indolines has been developed using DMSO as a catalyst and solvent. Mechanistic studies have revealed the important role of DMSO in the reaction. The method offers mild reaction conditions, short reaction time, broad substrate scope, a new application of DMSO, and scalability to gram-scale preparation without column chromatography.
Article
Chemistry, Multidisciplinary
Kang Wang, Yan Xu, Jianbo Wang
Summary: The palladium-catalyzed cyclizative borylation of allenyl ketones with diboron compounds is reported, which involves carbene boryl migratory insertion as the key step. This reaction shows mild conditions, good functional group tolerance, and broad substrate scope. It provides an efficient method for the assembly of diverse tri-substituted furyl boronates. Additionally, a series of transformations on the resultant multi-substituted furyl boronates yield various densely substituted furan derivatives in good yields, demonstrating the synthetic utility of this methodology.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Sudip Shit, Bipin Kumar Behera, Subhamoy Biswas, Anil K. K. Saikia
Summary: A metal-free Lewis acid-initiated protocol has been developed for the synthesis of highly substituted 3-(dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines. The reaction involves the formation of dihydrofuranylidene carbocation followed by intramolecular cyclization, leading to the desired products in moderate to good yields. The methodology can also be extended to the synthesis of 3-(dihydro-2H-pyran-3(4H)-ylidene)-isobenzofuran-1(3H)-imines, and furanylidene isobenzofuranones can be obtained in excellent yields through post synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sujeet Kumar, Km Kajol, Prakash Nayak, Amit Kumar, Chintakunta Ramesh
Summary: A palladium-catalyzed intramolecular direct heteroarylation of oxazole tethered beta-naphthols to access tetracyclic 4H-benzo[5,6]chromeno[3,4-d]oxazoles is reported. The reaction exhibits good to excellent yields with various functional groups. The resulting molecules show promising synthetic utility and UV/vis absorption and fluorescence emission properties.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Xiaohong Wang, Fengzhi You, Baojian Xiong, Lei Chen, Xuemei Zhang, Zhong Lian
Summary: In this study, a metal- and base-free 5-endo-trig sulfonylative cyclization was developed for the synthesis of sulfonylated pyrrolin-2-ones. The reaction proceeded in one pot with excellent regioselectivity and good-to-excellent yields. The method showed mild reaction conditions and broad substrate scope, as well as practicality demonstrated through scale-up reactions and synthetic applications.
Article
Chemistry, Organic
Jinling Liu, Yinghua Yu, Xueliang Huang
Summary: Deuterated compounds are important in pharmaceutical chemistry and the selective incorporation of deuterium atoms onto pharmacophore-containing compounds is of great interest. In this study, a concise method for constructing deuterated dibenzo-fused epsilon-lactones and epsilon-lactams through Pd-catalyzed carbene bridging C-D bond activation strategy was described. Deuterated ortho-bromobenzaldehydes were readily available reactants and deuterium atoms were selectively incorporated at the dibenylic position with high deuterated ratio.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Quan Zhou, Hai-Yan Yu, Yaqing Zhou, Jing-Ru Wei, Lei Wang
Summary: A concise and facile synthesis of 2-sulfonylated chromeno [4,3-c]pyrazol-4(2H)-ones or 2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-ones was developed via Cu(ii)-promoted oxidative cascade C-C/C-N bond formation. This protocol offers atom economy and good functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Neha Jha, Nandkishor Prakash Khot, Manmohan Kapur
Summary: The past decade has seen significant advancements in transition-metal-catalyzed C-H bond activation and carbene migratory insertion reactions, facilitating the construction of diverse arene/heteroarene scaffolds. Various transition-metal catalysts are utilized for easy access to substituted heterocycles, with key mechanistic pathways involving C-H activation, diazo insertion, and subsequent coupling reactions.
Article
Biochemistry & Molecular Biology
Manpreet Kaur, Vikrant Mehta, Aabid Abdullah Wani, Sahil Arora, Prasad Bharatam, Ashoke Sharon, Sandeep Singh, Raj Kumar
Summary: A new synthetic route for 1,4-dihydropyrazolo[4,3-b]indoles was reported, and the resulting compounds showed cytotoxicity against various cancer cell lines, potentially acting as selective inhibitors of Topo I or Topo II.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lucas G. Furniel, Radell Echemendia, Antonio C. B. Burtoloso
Summary: Efficient and enantioselective carbene-mediated insertion reactions from a sulfur ylide have been achieved, leading to the synthesis of thirty-seven alpha-arylglycine esters with enantiomeric ratios up to 92 : 8 (99 : 1 after recrystallization) using a copper-bifunctional squaramide cooperative catalysis approach. The protocol offers quick reaction times and high reaction yields up to 96%.
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Caijin Zeng, Shaoting Su, Songjia Fang, Huangfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel palladium-catalyzed three-component carbonylation reaction has been developed for the efficient assembly of 1,3-substituted maleimides from haloalkynes and simple anilines. The reaction exhibits high chemo- and regioselectivities, and operates under mild conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Organic
Douglass F. Taber
Summary: Direct functionalization of unactivated C-H bonds is becoming increasingly important in organic synthesis. Among the various methods, intramolecular alkylidene C-H insertion, which retains the absolute configuration, is one of the most versatile. This Review explores all examples of the use of intramolecular alkylidene C-H insertion in natural product synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Physical
Ayesha, Muhammad Bilal, Nasir Rasool, Samreen Gul Khan, Umer Rashid, Humaira Altaf, Imtiaz Ali
Summary: This review summarizes twelve years of successful indole synthesis using various palladium catalysts to establish carbon-carbon or carbon-nitrogen coupling, as well as the optimized conditions for these reactions.
Article
Chemistry, Multidisciplinary
Bingkai Yuan, Can Li, Yan Zhao, Oliver Groening, Xieyu Zhou, Pengfei Zhang, DanDan Guan, Yaoyi Li, Hao Zheng, Canhua Liu, Yiyong Mai, Peinian Liu, Wei Ji, Jinfeng Jia, Shiyong Wang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Wei Feng, Li Xu, Deng-Yuan Li, Pei-Nian Liu
Article
Chemistry, Multidisciplinary
Deng-Yuan Li, Ya-Cheng Zhu, Shi-Wen Li, Chen-Hui Shu, Pei-Nian Liu
Summary: This study achieved the on-surface post-functionalization of supramolecular polymers on gold surfaces, and discovered an enantioselective on-surface reaction induced by the chirality of the supramolecular polymers. Mechanistic analysis and DFT calculations revealed high enantioselectivity during the addition of ICBP to the chiral SP intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Deng-Yuan Li, Xia Qiu, Shi-Wen Li, Yin-Ti Ren, Ya-Cheng Zhu, Chen-Hui Shu, Xiao-Yu Hou, Mengxi Liu, Xing-Qiang Shi, Xiaohui Qiu, Pei-Nian Liu
Summary: Linear ladder phenylenes (LPs) chains were successfully synthesized on the Au(111) surface, achieving longer polymeric LPs that were previously inaccessible in solution due to improved chemoselectivity and orientation orderliness. By combining microscopy techniques, the atomic structure and electronic properties of the LP chains were characterized, revealing the charged state of chains on the NaCl layer with predicted indirect bandgap and antiferromagnetism in the polymeric LP chains.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Shi-Wen Li, Ruo-Xi Zhang, Li-Xia Kang, Deng-Yuan Li, Yu-Li Xie, Cheng-Xin Wang, Pei-Nian Liu
Summary: The study explores the construction of metal-organic networks (MONs) by the coordination self-assembly of isocyanides on Cu(111) and Ag(111) surfaces, showing that surface stereochemistry plays a crucial role in steering the structures. Nodes with heterotactic configurations are able to grow into larger subunits and form complex fractal structures.
Article
Chemistry, Multidisciplinary
Deng-Yuan Li, Ying Wang, Xiao-Yu Hou, Yin-Ti Ren, Li-Xia Kang, Fu-Hua Xue, Ya-Cheng Zhu, Jian-Wei Liu, Mengxi Liu, Xing-Qiang Shi, Xiaohui Qiu, Pei-Nian Liu
Summary: In this study, we report a novel [1+1+1] cycloaddition reaction for the synthesis of aza[3]radialenes on the Ag(111) surface, where the steric hindrance of the chlorine substituents guides the selective and orientational assembling of the isocyanide precursors. The atomic structure of the produced aza[3]radialenes is determined by combining scanning tunneling microscopy, non-contact atomic force microscopy, and time-of-flight secondary ion mass spectrometry. Furthermore, density functional theory calculations propose two reaction pathways, including synergistic and stepwise, revealing the role of the chlorine substituents in the activation of the isocyano groups via electrostatic interaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yan He, Heng Wang, Li Xu, Deng-Yuan Li, Ji-Hong Ge, Da-Fu Feng, Wei Feng, Gang Zou, Pei-Nian Liu
Summary: The study presents a step-economic strategy for the direct synthesis of bridged polycyclic skeletons by merging oxidative C-H annulation and cascade cycloaddition, achieving the one-pot construction of multiple carbon centers and carbon-carbon bonds. Mechanistic investigations revealed a cascade ring-opening, 1,5-sigmatropic rearrangement, and [4 + 2] cycloaddition process.
Article
Chemistry, Multidisciplinary
Cheng-Kun Lyu, Yi-Fan Gao, Zi-Ang Gao, Song-Yu Mo, Mu-Qing Hua, En Li, Shu-Qing Fu, Jia-Yan Chen, Pei-Nian Liu, Li Huang, Nian Lin
Summary: In this study, single-layer two-dimensional cMOFs were successfully synthesized using on-surface synthesis method, consisting of HAT molecules and metal atoms. The magnetic moments of different metal atoms were found to vary, which may be attributed to the conjugated core and coordination properties of HAT.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Can Li, Yu Liu, Yufeng Liu, Fu-Hua Xue, Dandan Guan, Yaoyi Li, Hao Zheng, Canhua Liu, Jinfeng Jia, Pei-Nian Liu, Deng-Yuan Li, Shiyong Wang
Summary: Topological defects in graphene materials introduce exotic properties, but collective magnetic behaviors originating from multiple topological defects remain a challenge. This study demonstrates that collective spin ordering can be achieved through engineering regular patterned topological defects in molecular graphenoids, providing a new platform for designing ferromagnetic spin chains and networks.
Article
Polymer Science
Shu-Qing Fu, Ming-Zhi Zhu, Boxin Xue, Pei-Nian Liu
Summary: A series of novel imidazolium-based cationic organic polymers (COPs) with various ionic capacities (ICs) and porosities were synthesized and applied to the adsorption of organic dyes. The results demonstrated a synergistic effect between IC and intrinsic porosity, where increasing the charge content was more effective than increasing the surface area.
Article
Polymer Science
Boxin Xue, Pan-Pan Huang, Ming-Zhi Zhu, Shu-Qing Fu, Ji-Hong Ge, Xingguang Li, Pei-Nian Liu
Summary: This study presents a highly efficient method to convert the C-H bonds of the aromatic ring of polystyrene (PS) into diverse functional groups. The combination of thianthrenation and thio-Suzuki-Miyaura coupling reaction allows for the synthesis of various functionalized PS with high selectivity and efficiency.
Article
Chemistry, Physical
Li-Xia Kang, Jian-Wei Liu, Shi-Wen Li, Can Li, Ying Wang, Qian Xu, Jun Hu, Honghe Ding, Junfa Zhu, Shiyong Wang, Deng-Yuan Li, Pei-Nian Liu
Summary: This study reports the ring-opening coupling reaction of epoxides on Ag surfaces and investigates the behavior of the reaction products on different surfaces. It is found that the Ag(110) surface promotes the formation of specific orientation in the polymer, while the Ag(111) surface leads to the formation of irregular polymers.
JOURNAL OF PHYSICAL CHEMISTRY C
(2022)
Article
Chemistry, Physical
Ya-Cheng Zhu, Fu-Hua Xue, Li-Xia Kang, Jian-Wei Liu, Ying Wang, Deng-Yuan Li, Pei-Nian Liu
Summary: Dendronized polymers (DPs) are composed of a linear polymeric backbone with dendritic side chains, and the fine-tuning of the functional groups in the side chains enriches the structural versatility and imparts novel physical properties to DPs. In this study, the first on-surface synthesis of DPs on Au(111) was achieved via postfunctionalization, and the surface confinement effects on the planar conformation and chiral configurations were characterized.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Jie Wang, Qing -Yang Li, Shan -Shan Wang, Xin-Yan Wu, Xingguang Li, Pei-Nian Liu
Summary: We have reported a novel rhodium-catalyzed rearrangement reaction involving N-substituted 2-thiopyridones and diazoesters. This reaction proceeds through the rhodium-catalyzed formation of sulfur ylides, followed by a direct C-N bond cleavage, achieving N-to-C 1,4-pyridyl migration. The protocol can be used to synthesize various thiopyridines with tetrasubstituted carbon stereocenters in moderate to excellent yields, expanding the transformation pattern of sulfur ylide intermediates in rearrangement reactions.
Article
Chemistry, Multidisciplinary
Gucheng Zhu, Yashi Jiang, Ying Wang, Bing-Xin Wang, Yuqiang Zheng, Yufeng Liu, Li-Xia Kang, Zhanbo Li, Dandan Guan, Yaoyi Li, Hao Zheng, Canhua Liu, Jinfeng Jia, Tao Lin, Pei-Nian Liu, Deng-Yuan Li, Shiyong Wang
Summary: A group of nitrogen-doped nanographenes (N-NGs) with atomic precision are fabricated on Au(111) through a combination of reactions, and the presence of collective quantum magnetism in N-NGs is revealed through high-resolution scanning probe microscopy measurements. The mechanism of magnetic exchange interaction of N-NGs is also compared with their pure hydrocarbon counterparts. These findings demonstrate the possibility of bottom-up synthesis of ordered quantum phases through the utilization of N-NGs to fabricate low-dimensional extended graphene nanostructures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
