Article
Chemistry, Multidisciplinary
Marti Garcon, Nicolette Wee Mun, Andrew J. P. White, Mark R. Crimmin
Summary: This study demonstrates a new method of transforming C-H bonds into C-Zn bonds using a palladium catalyst and zinc hydride reagent, which has been successfully applied to various types of arenes with high selectivity. Mechanistic studies show that heterometallic complexes play a crucial role in the catalytic process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xiaolin Shi, Zemin Wang, Yuxiu Li, Xiaowei Li, Xiangqian Li, Dayong Shi
Summary: The study reports a challenging palladium-catalyzed remote C4-H phosphonylation of indoles using a radical approach. The method not only provides a new synthetic pathway, but also unexpectedly obtained C6-phosphonylated indoles, suggesting a potential strategy for future cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Till Schmidt-Raentsch, Hendrik Verplancke, Jonas N. Lienert, Serhiy Demeshko, Matthias Otte, Gerard P. Van Trieste, Kaleb A. Reid, Joseph H. Reibenspies, David C. Powers, Max C. Holthausen, Sven Schneider
Summary: In this study, the synthesis of a formal terminal nitride complex of palladium was reported, and it was characterized through photocrystallography, magnetism, and computational methods. Based on this complex, a photocatalytic protocol for aldehyde C-H trimethylsilylamidation was developed, which exhibited inverted nucleophilic selectivity. This first example of catalytic C-H nitrogen atom transfer has significant implications for obtaining primary amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sif T. Linde, Vasco Corti, Vibeke H. Lauridsen, Johannes N. Lamhauge, Karl Anker Jorgensen, Nomaan M. Rezayee
Summary: This article presents a method for obtaining a versatile chiral biaryl structure through C-H halogenation reactions using high-valent Pd catalysis and chiral transient directing groups. The method is scalable, moisture and air insensitive, and in some cases, requires low Pd-loadings of only 1 mol%. Chiral mono-brominated, dibrominated, and bromochloro biaryls can be prepared in high yield and excellent stereoselectivity, serving as building blocks for various reactions with orthogonal synthetic handles.
Article
Chemistry, Multidisciplinary
Ling Dai, Shuling Yu, Yinlin Shao, Renhao Li, Zhongyan Chen, Ningning Lv, Jiuxi Chen
Summary: In this study, an efficient protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton from simple arenes and functionalized aliphatic nitriles was achieved for the first time. The reaction proceeds efficiently under redox-neutral conditions with high atom-economy, suggesting that C-H bond cleavage of the simple arenes might be the rate-determining step.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Nahiane Pipaon Fernandez, Gregory Gaube, Kyla J. Woelk, Mathias Burns, Damian P. Hruszkewycz, David C. Leitch
Summary: We present a new method for direct C-C bond formation using tandem C-O/C-H activation mediated by palladium catalyst. This approach allows for base-free direct C-H alkenylation by combining C-O oxidative addition at enol pivalates and concerted metalation-deprotonation of functionalized heterocycles. Mechanistic studies show that C-O oxidative addition is reversible and C-H activation occurs directly from the Pd(II) C-O oxidative addition product. In situ P-31 NMR spectroscopy reveals that (Cy3P)(2)Pd-(alkenyl)(OPiv) species is the predominant catalyst resting state during the reactions.
Article
Chemistry, Multidisciplinary
Gouranga Naskar, Masilamani Jeganmohan
Summary: This paper describes a palladium-catalyzed [3+2] annulation reaction of substituted benzoic acids with maleimides, leading to tricyclic heterocyclic molecules with a free carboxylic group in a highly atom- and step-economical manner. The reaction involves dual C-H bond activation, including C(sp(3))-H activation at the benzylic position and C(sp(2))-H bond activation at the meta position of substituted aromatics. The success of this protocol relies on the presence of an external ligand, MPAA. Additionally, decarboxylation and esterification of the free carboxylic acid group in the observed products were conducted.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Jyoti Dhankhar, Micha D. Hofer, Anthony Linden, Ilija Coric
Summary: This article presents a new selectivity mode for C-H arylation reactions, which is the preference for C(sp(2))-H activation next to alkyl groups. The study results indicate that this preference is related to the non-covalent interactions between the catalyst and the substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Mohammad Aslam, Shreedhar Devkota, Sana Jamshaid, Yong Rok Lee
Summary: A synthetic strategy for the installation of diversely functionalized quinones at the C4 position of indoles has been developed. This method provides a rapid and efficient route to a variety of 4-quinonylindoles and biologically interesting bis(indol-4-yl)quinones.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Li-Yun Guo, Qing Li, Yu-Tao Liu, Lin Li, Yu-Qing Ni, Yang Li, Fei Pan
Summary: A palladium-catalyzed method for direct alkynylation of unactivated alkenes via C-H activation, assisted by 8-aminoquinoline, has been successfully developed. This method is applicable to both internal and terminal unactivated alkenes, showing broad functionality tolerance, good regio- and diastereoselectivity, and providing an alternative approach for constructing conjugated 1,3-enynes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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, Multidisciplinary
Ellen Y. Aguilera, Melanie S. Sanford
Summary: This paper presents a new method for transannular functionalization of the gamma-C-H bonds in alicyclic amines. By pre-complexing the substrate with Pd before adding an oxidant, high selectivity can be achieved for installing various heteroatom functional groups at the gamma position.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Luo-Yan Liu, Zhoulong Fan, Md Emdadul Hoque, Shaoqun Qian, Guangrong Meng, Nikita Chekshin, Keita Tanaka, Jennifer X. X. Qiao, Kap-Sun Yeung, Jin-Quan Yu
Summary: Remote C-H functionalization of heterocyclic biaryls is crucial in synthesis and medicinal chemistry. New catalytic templates have been developed to functionalize the hindered ortho-C-H bonds of heterobiaryls, using directing heteroatom at the meta- or para-positions, with unprecedented site-selectivity. This protocol overcomes steric and electronic effects, allowing olefination of sterically hindered heterobiaryls.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Rui Liu, Meng-Lan Shen, Lian-Feng Fan, Xiao-Le Zhou, Pu-Sheng Wang, Liu-Zhu Gong
Summary: Allylamines are important for synthesizing bioactive compounds and can be obtained through the palladium-catalyzed allylic C-H amination of 1,4-dienes. This reaction favors the formation of thermodynamically unstable Z-allylamines with aromatic amines. Aliphatic cyclic amines can also participate, but linear dienyl allylic amines are the main products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Dominik Lichte, Nico Pirkl, Gregor Heinrich, Sayan Dutta, Jonas F. Goebel, Debasis Koley, Lukas J. Goossen
Summary: This study demonstrates the achievement of para-C-H arylation of non-activated aryl halides with anilines using a base-assisted metalla-tautomerism approach. The challenge of directing functionalization towards the furthest C-H group has been overcome.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chuang Niu, Zheng-Chun Yin, Wei-Feng Wang, Xinmin Huang, Dian-Bing Zhou, Guan-Wu Wang
Summary: In this study, the conversion of [60]fullerene-fused lactones to ketones has been achieved in excellent yields using triflic anhydride as an unusual reductant under aerobic conditions. The thermal retro Baeyer-Villiger reaction from lactones to ketones is unprecedented. Furthermore, unique ring-opened peroxy [60]fullerene derivatives can be synthesized through electrochemical reactions of the synthesized [60]fullerene-fused ketones.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Zheng-Chun Yin, Chuang Niu, Mingjie Li, Wen-Rui Liu, Guan-Wu Wang
Summary: Regioselective electrochemical hydroalkylations of [60]fullerene-fused furochromenone with alkyl halides under different acidic conditions unexpectedly afford three types of tetra-functionalized [60]fullerene derivatives in high yields. These products have been characterized by spectroscopic data and single-crystal X-ray analysis, and two of them show diagnostic UV-vis spectra. A plausible reaction mechanism has been proposed to elucidate the formation of hydroalkylation products in the presence of different acids.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Qing-Song Liu, Wen-Jie Qiu, Chuang Niu, Guan-Wu Wang
Summary: A novel and efficient palladium-catalyzed C-H activation reaction was developed for the synthesis of [60]fullerene-fused phosphinolactones. The reaction showed high selectivity and yield of the desired products, which could be further transformed using electrochemical methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hui Xu, Ming-Jun Li, Hong Chen, Fei-Hong Huang, Qi-Yue Zhu, Guan-Wu Wang, Ze Zhang
Summary: A novel and efficient multi-component reaction has been developed for the synthesis of polysubstituted pyrroles. This protocol offers several advantages including mild reaction conditions, broad substrate scope, and high efficiency.
Editorial Material
Multidisciplinary Sciences
Xing -Xing Yan, Chuang Niu, Zheng-Chun Yin, Wen-Qiang Lu, Guan-Wu Wang
Summary: This paragraph is about the copyright statement, indicating the ownership of the copyright and reserving all rights.
Review
Oncology
Guanwu Wang, Lara Rosaline Heij, Dong Liu, Edgar Dahl, Sven Arke Lang, Tom Florian Ulmer, Tom Luedde, Ulf Peter Neumann, Jan Bednarsch
Summary: This systematic review evaluated the association between single-nucleotide polymorphisms (SNPs) and cholangiocarcinoma (CCA), focusing on tumorigenesis and prognosis. Based on 34 studies, a total of 43 SNPs in 32 genes associated with CCA risk, metastatic progression, and overall prognosis were identified. The study comprehensively described the mechanisms and potential clinical implications associated with these SNPs. The findings suggest that multiple SNPs play different roles at different stages of CCA and may serve as biomarkers for guiding treatment and assessing oncological risk.
Article
Chemistry, Multidisciplinary
Zheng-Chun Yin, Mingjie Li, Chuang Niu, Wei-Feng Wang, Wen-Rui Liu, Qian-Wen Zhang, Guan-Wu Wang
Summary: This study achieves the reductive electrosynthesis of heterocycle-fused fulleroids from fullerotetrahydropyridazines and electrophiles in the presence of a trace amount of oxygen, with concurrent ring contraction and expansion reactions. Depending on the electrophiles used, different regioselective formations of heterocycle-fused fulleroids are achieved. The reaction proceeds through multiple steps, and the structures of the synthesized fulleroids have been determined and their high regioselectivities rationalized by theoretical calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Gang Shao, Chuang Niu, Hong-Wei Liu, Huan Yang, Jun-Shen Chen, Yang-Rong Yao, Shangfeng Yang, Guan-Wu Wang
Summary: The mechanochemical cascade reaction of [60]fullerene with various compounds has been investigated under solvent-free and ball-milling conditions. This method provides an efficient way to obtain [60]fullerene-fused cyclopentanes, with advantages of good substrate scope, short reaction time, and solvent-free and ambient reaction conditions. Additionally, these fullerene products have been successfully applied as efficient cathode interlayers in inverted planar perovskite solar cells.
Article
Chemistry, Organic
Peng-Cheng Cui, Zheng-Chun Yin, Guan-Wu Wang
Summary: The visible-light-promoted C4-selective phosphorylation of unprefunctionalized pyridine and quinoline derivatives has been achieved. This Minisci-type protocol offers highly regioselective access to C4-phosphorylation products with good functional group tolerance and moderate to good yields via cross dehydrogenation coupling under mild conditions. Mechanistic studies demonstrate that the C4-phosphorylation products are obtained through a radical pathway.
Article
Materials Science, Multidisciplinary
Mingjie Li, Tai An, Zongliang Ou, Ke Jin, Zhiwen Jin, Keyou Yan, He Tian, Wentao Wang, Shangfeng Yang, Guan-Wu Wang, Qiuling Song, Zuo Xiao, Liming Ding
Summary: A copolymer donor PBDTTPTP based on a tetracyclic bislactone unit, thieno[2',3':5,6]pyrano[3,4-d]thieno[3,2-b]pyran-4,9-dione (TPTP), was developed. The copolymer PBDTTPTP showed a deep HOMO level of -5.60 eV, a small optical bandgap of 1.65 eV and a good hole mobility of 6.57 x 10(-4) cm(2) V-1 s(-1) due to the strong electron-withdrawing properties and good coplanarity of TPTP. STOPVs based on PBDTTPTP and N3 exhibited a high light utilization efficiency of 4.38%, a power conversion efficiency of 12.26%, and an average visible light transmittance of 35.7%.
MATERIALS ADVANCES
(2023)
Article
Surgery
Carlos Constantin Otto, Guanwu Wang, Anna Mantas, Daniel Heise, Philipp Bruners, Sven Arke Lang, Tom Florian Ulmer, Ulf Peter Neumann, Lara Rosaline Heij, Jan Bednarsch
Summary: This study investigated the association between time to surgery (TTS) and oncological outcomes in HCC patients. The results showed that TTS was not associated with tumor recurrence or overall survival in surgically treated HCC patients.
LANGENBECKS ARCHIVES OF SURGERY
(2023)
Article
Chemistry, Physical
Pengqi Li, Xianyi Meng, Ke Jin, Zhiwei Xu, Jianqi Zhang, Lixiu Zhang, Chuang Niu, Furui Tan, Chenyi Yi, Zuo Xiao, Yaqing Feng, Guan-Wu Wang, Liming Ding
Summary: The emergence of Y6-type nonfullerene acceptors has greatly improved the power conversion efficiency of organic solar cells. However, the impact of different structural features on the excellent photovoltaic performance is still debated. In this study, two new Y6-like acceptors were designed, and it was found that the banana-shaped molecular structure is likely to be the determining factor for achieving high photovoltaic performance.
Article
Chemistry, Multidisciplinary
Guanhua Zong, Mingjie Li, Ke Jin, Zhiwei Xu, Lixiu Zhang, Ning Ma, Jilin Wang, Guan-Wu Wang, Zuo Xiao, Liming Ding
Summary: By synthesizing two low-bandgap ADA small molecule acceptors with asymmetric side chains, this study demonstrates that introducing asymmetric side chains at different positions of the core unit can enhance the molecular properties and efficiency of the acceptor.
MATERIALS CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yi-Tan Su, Zheng-Chun Yin, Guan-Wu Wang
Summary: In this study, a palladium-catalyzed three-component reaction was developed for the synthesis of 1,4-aminoarylated [60]fullerene derivatives under mild conditions. Moreover, further transformations were achieved in the presence of ferric chloride.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Qing-Song Liu, Wen-Jie Qiu, Wen-Qiang Lu, Guan-Wu Wang
Summary: A novel and efficient copper-mediated [3 + 2] heteroannulation reaction has been developed for the synthesis of fullerooxazoles. The reaction mechanism involves unique C-CN and N-OH bond cleavages and subsequent C-OH bond formation for N-hydroxybenzimidoyl cyanides. Furthermore, the formed fullerooxazoles can be further electrochemically transformed into amidated 1,2-hydrofullerenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
