Article
Chemistry, Organic
Xin Geng, Heng He, Andrey Shatskiy, Elena V. Stepanova, Gregory R. Alvey, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: A straightforward synthetic approach for the construction of phenanthridin-6-(5H)-one skeletons is reported. Palladium catalysis is used to provide controlled access to a range of functionalized phenanthridin-6-(5H)-ones in yields of 59-88%. Plausible reaction pathways are proposed based on mechanistic experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sunil Kumar Sunnam, Jitendra D. Belani
Summary: Recent research has explored arylation via ortho C-H activation with the aid of directing groups, leading to the development of a palladium-catalyzed C-H arylation using 8-aminoquinoline as a bidentate directing group. This method selectively provides C-H arylation products, unlike previous methods where cyclization to isoquinolones was observed. Additionally, sequential C-H functionalization was observed under specific conditions, leading to C-H olefination with the aryl group introduced from the aryne precursor.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Tyler G. Saint-Denis, Nelson Y. S. Lam, Nikita Chekshin, Paul F. Richardson, Jason S. Chen, Jeff Elleraas, Kevin D. Hesp, Daniel C. Schmitt, Yajing Lian, Chan Woo Huh, Jin-Quan Yu
Summary: Enantioselective C(sp(3))-H activation has attracted significant interest, but the mechanisms responsible for enantioselection remain unclear. This study found extreme sensitivity differences in two substrate classes, leading to high enantiomeric ratios for thioether-directed-C(sp(3))-H arylation. The exploitation of transient chirality at sulfur was key to achieving stereochemical information transfer from ligand backbone to substrate carbons.
Article
Chemistry, Organic
Hemanta Hazarika, Dhiraj Dutta, Sanfaori Brahma, Babulal Das, Pranjal Gogoi
Summary: A Pd-catalyzed alkyne and aryne annulation strategy via C-H activation has been successfully used for the synthesis of pi-extended coumarins. This strategy provides a wide range of pi-extended coumarins with good functional group compatibility and moderate to good yields. The photophysical properties of the synthesized pi-extended coumarins have been evaluated, showing interesting fluorescent properties.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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.
Review
Chemistry, Applied
Xue-Song Zhang, Ya-Ping Han, Yuecheng Zhang, Yong-Min Liang
Summary: Elaborated molecular architectures, such as complex carbocycles, heterocycles, and polycyclic structures, are important organic compounds found in natural products, medicinal molecules, and functional materials. The development of efficient and selective methods for constructing these compounds from readily available starting materials is a major challenge in synthetic methodology. Transition-metal-catalyzed transformations involving Heck reaction have emerged as a powerful approach for accessing sophisticated polycyclic skeletons, streamlining the drug discovery process. This review summarizes the latest advances in transition-metal-catalyzed transformations involving Heck reaction, including six categories: Heck/Sonogashira tandem reaction, Heck/Suzuki tandem reaction, Heck/Heck tandem reaction, Heck/Hiyama tandem reaction, Heck/Cacchi tandem reaction, and Heck/C-H bond functionalization tandem reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Bing Xu, Quanpu Wang, Chao Fang, Zhan-Ming Zhang, Junliang Zhang
Summary: This review summarizes the latest advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years. The review is organized into thirteen sections based on the different types of transformations involved. Chiral palladium catalysts have shown outstanding features in promoting a plethora of enantioselective cyclization reactions, providing convenient access to structurally diverse chiral carbo- and hetero-cycles.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Sebastian Martinez-Flores, Cesar A. Mujica-Martinez, Luis A. Polindara-Garcia
Summary: A Pd(II)-catalyzed C(sp(2)/sp(3))-H bond arylation protocol has been developed for the synthesis of ortho-diaryl, ortho-mono-aryl, and biaryl-diarylmethane-glycinamide derivatives bearing picolinamide as a directing group. Mechanistic details were investigated through computational modeling using DFT calculations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Raju S. Thombal, Peter Yuosef M. Rubio, Daesung Lee, Debabrata Maiti, Yong Rok Lee
Summary: Metal catalyzed cascade C-H activation/annulation is a highly promising approach for the construction of aromatic and heteroaromatic compounds. Pd-complexes play a crucial role in this method, enabling high catalytic efficiency through the activation of molecules bearing a directing group.
Article
Chemistry, Applied
Dipak B. Deokar, Soumi Laha, B. Sridhar, Dharmendra Kumar Tiwari, Pravin R. Likhar
Summary: A palladium-catalyzed coupling reaction followed by dual annulation has been developed for the synthesis of various triazolo/pyrrolo fused benzofuro-quinolines from readily available starting materials. This method involves palladium-catalyzed Sonogashira coupling, benzan-nulation, and C-H activation triggered second annulation reaction cascades in a single pot. The polycyclic compound formed by this method consists of three different heterocyclic structures: benzofuran, quinoline, and triazole/pyrrole. The method provides a simple access to obtain a range of fused benzofurotriazalo/pyrroloquinolines in good to moderate yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Jean Le Bras, Jacques Muzart
Summary: The review mainly focuses on dehydrogenative Heck reactions published since 2010, highlighting the diversity of procedures, mechanisms, and intermediates proposed, along with some personal comments.
CURRENT ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Ken Kamikawa
Summary: Although arynes are usually fleeting intermediates, they are highly useful in synthetic applications due to their ability to introduce aromatic rings and form new bonds at multiple sites. Asymmetric catalysis for capturing arynes has been a challenging goal in aryne chemistry, as it requires sufficient interactions between the short-lived arynes and reactive intermediates in a stereo-controlled manner. This review highlights recent advances in asymmetric reactions using arynes, including diastereoselective, enantioselective, and catalytic enantioselective reactions.
NATURE REVIEWS CHEMISTRY
(2023)
Article
Chemistry, Physical
Ana G. Herraiz, Nicolai Cramer
Summary: Catalytic enantioselective C-H functionalization has become a tool for creating stereogenic centers, but remains a challenge. A three-component C-H functionalization catalyzed by an earth-abundant Co(III) complex with high enantioselectivity has been described, providing a rapid access to substituted beta-hydroxyketones. The outlined reactivity of (CpCo)-Co-x(III) catalysis shows a higher and exploitable propensity for selective additions across carbonyls compared to Rh(III) chemistry.
Article
Chemistry, Physical
Wei Hao, Katherine L. Bay, Caleb F. Harris, Daniel S. King, Ilia A. Guzei, Michael M. Aristov, Zhe Zhuang, R. Erik Plata, David E. Hill, K. N. Houk, John F. Berry, Jin-Quan Yu, Donna G. Blackmond
Summary: This study investigated the influence of chiral monoprotected aminoethyl amine (MPAAM) ligands on enantioselective Pd-catalyzed arylation of strong cyclopropane C(sp(3))-H bonds. The results revealed a subtle impact of ligand structure on reaction kinetics and mechanism, as well as a negative dependence of ligand concentration on reaction rate. These findings demonstrate the importance of ligand design in catalytic reactions.
Review
Chemistry, Organic
Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan
Summary: Dearomatization reaction is a popular research area in organic chemistry, which can build highly functionalized three-dimensional molecules from aromatic compounds. This review discusses the mechanisms and various synthetic protocols of dearomatization reactions involving arynes, as well as provides insights and outlooks on this rapidly developing field.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Plant Sciences
Zu-Jun Que, Jia-Liang Yao, Zhi-Yi Zhou, Pan Yu, Bin Luo, He-Gen Li, Jia-Xiang Liu, Hong-Xi Xu, Jian-Hui Tian
Summary: Jinfukang may prevent lung cancer metastasis by enhancing the clearance of CTCs in the peripheral blood by NK cells, providing evidence for the anti-metastasis effect of Jinfukang.
JOURNAL OF ETHNOPHARMACOLOGY
(2021)
Article
Chemistry, Medicinal
Qing-Wei Fang, Wen-Wei Fu, Jin-Ling Yang, Yue Lu, Jiang-Cheng Chen, Pei-Ying Wu, Xue Zhang, Hong-Xi Xu
Summary: In this study, a new compound, crocusatin M, and three new glycosidic compounds, crocusatins N-P, were isolated from the dried stigmas of Crocus sativus. The structures of the new compounds were determined by spectroscopic analysis, with compounds 1 and 4 showing weak anti-inflammatory activities.
JOURNAL OF NATURAL MEDICINES
(2022)
Correction
Toxicology
Xing Wang, Yu-Jie Lou, Ming-Xing Wang, Yun-Wei Shi, Hong-Xi Xu, Ling-Dong Kong
TOXICOLOGY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Minghao Feng, Ivan Mosiagin, Daniel Kaiser, Boris Maryasin, Nuno Maulide
Summary: This study presents a novel strategy for the diastereo- and enantioselective synthesis of fi-amino amides through the direct coupling of carboxamides with ketimines. This innovative approach addresses key challenges in the Mannich reaction process, showcasing its significance in synthetic and biological chemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Minghao Feng, Haoqi Zhang, Nuno Maulide
Summary: Compared to ketones and carboxylic esters, amides have traditionally been considered as less reactive members of the carbonyl family. However, recent research has shown that selective activation of amides under mild conditions is possible. This Minireview highlights the latest advances in this field, showcasing new strategies and breakthroughs in amide activation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Minghao Feng, Roberto Tinelli, Ricardo Meyrelles, Leticia Gonzalez, Boris Maryasin, Nuno Maulide
Summary: This study reports a practical method for the synthesis of alpha-amino acid derivatives via direct hydrative amination of activated alkynes using sulfinamides as the nitrogen source under mild conditions. Computational studies suggest that the reaction is enabled by a new type of sulfonium [2,3]-sigmatropic rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Anthony J. J. Fernandes, Ana Sirvent, Eleonora Spinozzi, Saad Shaaban, Nuno Maulide
Summary: We present a simple method for the direct amination of unfunctionalized, native carbonyls (amides and ketones) by transferring a free amino group (NH2) from a commercially available nitrogen source. Mild conditions enable the production of primary a-amino carbonyls, allowing for diverse in situ functionalization reactions, such as peptide coupling and Pictet-Spengler cyclization, that take advantage of the presence of the unprotected primary amine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Analytical
Simin Chen, Man Yuan, Yingling Zhang, Yu Xu, Hongxi Xu
Summary: The aim of this study was to establish a method for the quality control of Fuzhuan brick tea for stable production. Ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry was used to identify Fuzhuan brick tea, and the major components were chosen for further quantitative analysis. Subsequently, a quantification method was developed using ultra-high-performance liquid chromatography coupled with triple-quadrupole mass spectrometry, and its reliability was verified through methodological validation. A total of 30 compounds were identified, including catechins, flavonoids, alkaloids, and fatty acids. The established method was reliable for methodological validation and was applied to the quantitative analysis of Fuzhuan brick tea. This study provides a fundamental basis for the quality control and further studies on the component analysis of Fuzhuan brick tea.
JOURNAL OF SEPARATION SCIENCE
(2023)
Article
Chemistry, Analytical
Gan Chen, Hong Zhang, Jiaming Jiang, Simin Chen, Hongmei Zhang, Gongmin Zhang, Changwu Zheng, Hongxi Xu
Summary: This study aimed to differentiate mountain-cultivated ginseng by age using LC-MS analysis and machine learning models. The study successfully predicted the age group of ginseng samples based on identified biomarkers.
JOURNAL OF SEPARATION SCIENCE
(2023)
Article
Anatomy & Morphology
Gong-Min Zhang, Qing Huang, Gan Chen, Man Yuan, Chang-Wu Zheng, Hong-Mei Zhang, Hong-Xi Xu
Summary: A new method was established to determine the age of Panax ginseng, which is important for assessing its market value and medical effects.
MICROSCOPY RESEARCH AND TECHNIQUE
(2023)
Review
Biochemistry & Molecular Biology
Jiaqi Tan, Hongmei Zhang, Li Zhang, Hongxi Xu
Summary: Ginseng has been used as both a traditional medicine and food for thousands of years, but there are concerns in China about the potential adverse effects of long-term or excessive use, known as Shanghuo. This review explores the relationship between ginseng and Shanghuo from the perspectives of traditional Chinese medicine (TCM) and modern science. It is believed that ginseng-induced Shanghuo is mainly driven by the hot property of the drug, and it may be related to energy metabolism and the endocrine, immune, and cardiovascular systems. The study also discusses the potential role of specific compounds in ginseng, such as ginsenosides, in inducing Shanghuo.
Article
Biochemical Research Methods
Xiaomei Luo, Man Yuan, Ping Lu, Xuanlei Zhong, Yibo Zhang, Yang Li, Zhichao Xi, Hongmei Zhang, Songlin Li, Hongxi Xu
PHYTOCHEMICAL ANALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Lea Madegard, Margaux Riomet, Manon Louis, Pier Alexandre Champagne, Gregory Pieters, Davide Audisio, Frederic Taran
Summary: In this study, a methodology for chlorination of iminosydnones is described, and the beneficial effect of this modification on the reactivity of these mesoionic dipoles in strain-promoted cycloaddition reactions is demonstrated. The new iminosydnones are used for bioorthogonal release of drugs containing amide, urea, and sulfonamide, with notable success in releasing drugs containing a terminal amide function.
CHEMICAL COMMUNICATIONS
(2022)
Review
Biochemistry & Molecular Biology
Yee Lin Phang, Song Liu, Changwu Zheng, Hongxi Xu
Summary: Natural products containing a phloroglucinol motif have significant medicinal value and biological activities. Recent studies have focused on synthetic approaches to these compounds, which have been widely used in treatment and clinical trials.
NATURAL PRODUCT REPORTS
(2022)
Article
Biochemistry & Molecular Biology
Jia-Ming Jiang, Gan Chen, Yu-Yu Chen, Shi-Jie Wan, Si-Min Chen, Han-Gui Ren, Zhi-Xiu Lin, Hui Feng, Hong Zhang, Hong-Xi Xu
Summary: Antivirulence therapy using Chinese Materia Medica, particularly the compound tanshinone IIB (TNB) found in Salvia miltiorrhiza Bunge, shows promising potential in combating Staphylococcus aureus infections by reducing hemolytic activity and abscess formation in organs through interference with the accessory gene regulator quorum sensing system.
