Article
Chemistry, Multidisciplinary
Chao Liu, Xiangwen Tan, Lingzhi Zhan, Yaru Jing, Wanqing Wu, Zhuofeng Ke, Huanfeng Jiang
Summary: A novel and efficient strategy for synthesizing fused benzo-aza-oxa-[5-6-5] tetracycles with high yields and diastereoselectivities has been demonstrated. This strategy involves the synthesis of functionally divergent anilines and 3-butenoic acid with five chemical bonds constructed. Control experiments and DFT calculations were performed to support the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Han-Jun Ai, Fengqian Zhao, Hui-Qing Geng, Xiao-Feng Wu
Summary: The letter discusses a generic method for the synthesis of linear thioesters through palladium-catalyzed thiocarbonylation of alkenes. This approach allows for the straightforward production of desired thioesters from readily available alkenes with moderate to good yields.
Article
Chemistry, Applied
Jiaqing Xu, Wangyu Shi, Min Liu, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo
Summary: A palladium-catalyzed [4+2] cycloaddition reaction has been developed for the efficient synthesis of tetrahydropyran derivatives with good selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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, Physical
Rei Matsuura, Malkanthi K. Karunananda, Mingyu Liu, Nhi Nguyen, Donna G. Blackmond, Keary M. Engle
Summary: This study investigated the mechanism of Pd(II)-catalyzed E/Z isomerization of unactivated olefins using a variety of methods. It was found that the directing group can stabilize and monitor previously undetectable intermediates, supporting isomerization occurring through a monometallic nucleopalladation mechanism.
Article
Chemistry, Organic
Aranya Das, Sudipto Debnath, Poulami Hota, Tuluma Das, Dilip K. Maiti
Summary: Unprecedented metal-free cyclization catalysis reactions are developed to synthesize 3-amino-4-benzoyl biphenyls and arylacridones with high atom economy. Catalytic K2CO3 is used to achieve rapid dual C-C-coupled cyclization between beta-keto enamines and cinnamaldehydes, while molecular I-2 acts as a catalyst for C(sp(2))-H functionalized C-N bond-forming cyclization to yield valuable arylacridones. Plausible mechanisms for the new cyclization reactions are predicted through control experiments and ESI-MS analyses.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qikai Sun, Huixing Zhang, Quanquan Wang, Tianjiao Qiao, Gang He, Gong Chen
Summary: A new strategy has been developed for the stereoselective synthesis of C-vinyl glycosides, using Pd-catalyzed directed C-H glycosylation. This method offers a broadly applicable approach to streamline the synthesis of complex C-vinyl glycosides with high efficiency and excellent regio- and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Grace L. Trammel, Abby C. Kerlin, Christian Zachau, M. Kevin Brown
Summary: The synthesis of (+/-)-phyltetralin is described, featuring a diastereoselective Cu/Pd-catalyzed arylboration reaction and a Matteson homologation.
Article
Chemistry, Multidisciplinary
Qiuyu Li, Jiajia Li, Jie Zhang, Shu Wu, Yu Zhang, Aijun Lin, Hequan Yao
Summary: A palladium-catalyzed asymmetric intramolecular alkene-alkyne coupling reaction has been developed for the synthesis of enantionenriched bicyclo[3.2.1]octadienes. The products exhibit an unusual iodination-induced 1,2-acyl migration, leading to the formation of iodinated bicyclo[3.2.1]octadienes with three vicinal stereocenters. The enone and isolated olefin motifs in the products provide versatile handles for further elaboration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Sidi Cheng, Yu Luo, Ting Yu, Jing Li, Chunfang Gan, Shuang Luo, Qiang Zhu
Summary: An unactivated alkene was successfully subjected to 1,2-difunctionalization through a palladium-catalyzed four-component cascade reaction, leading to the convenient synthesis of acetamides with various substituents and pyrrolo-fused heterocycles.
Review
Chemistry, Organic
Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang
Summary: This article summarizes the methods of alkene isomerization, which can efficiently construct multi-substituted alkenes via the stereoselective or positional-selective modulation of carbon-carbon double bonds. These methods have important applications in the synthesis of drug molecules and natural products.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hailiang Pang, Dong Wu, Guoyin Yin
Summary: A palladium-catalyzed migratory diarylation of unconjugated cyclohexadiene has been discovered, showing high 1,3-regioselectivity and exclusive cis-diastereoselectivity. The excellent selectivity suggests that the olefin remains bound to the palladium during chain-walking, providing a simple method for the synthesis of 1,3-diaryl-substituted cyclohexanes.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qile Wang, Thomas R. Hoye
Summary: The study presents a novel Cu(I)-catalyzed reaction for introducing different substituents onto benzyne molecules, showing potential for various applications.
Article
Chemistry, Multidisciplinary
Ren-Rui Xu, Xiuyu Fang, Xinxin Qi, Xiao-Feng Wu
Summary: A general and straightforward strategy for the synthesis of thioester-substituted oxindoles via a palladium-catalyzed thiocarbonylative cyclization process has been developed. Thioester-substituted oxindoles were obtained in moderate to high yields using sulfonyl chlorides as the sulfur source. Both aryl and alkyl sulfonyl chlorides were well tolerated, and Mo(CO)(6) played a dual role as both a CO source and a reductant in this approach.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Zicong Chen, Chau Ming So
Summary: Palladium-catalyzed cross-coupling reactions are essential for C-C bond formation, with new catalyst development driving progress in the field. A new easily accessible phenylpyrazole phosphine ligand was developed in this study, leading to an efficient catalyst for cross-coupling reactions. This method offers a practical alternative for synthesizing multi-substituted alkenes under mild conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shantanu Mishra, Shadi Fatayer, Saleta Fernandez, Katharina Kaiser, Diego Pena, Leo Gross
Summary: We report the on-surface synthesis of a non-benzenoid triradical through dehydrogenation of truxene (C27H18) on coinage metal and insulator surfaces. The final product truxene-5,10,15-triyl (1) retains its open-shell quartet ground state on a two monolayer-thick NaCl layer on a Cu(111) surface, and its frontier orbital densities correspond to spin-split singly occupied molecular orbitals.
Article
Geochemistry & Geophysics
Katharina Kaiser, Fabian Schulz, Julien F. Maillard, Felix Hermann, Iago Pozo, Diego Pena, H. James Cleaves, Aaron S. Burton, Gregoire Danger, Carlos Afonso, Scott Sandford, Leo Gross
Summary: Researchers used high-resolution atomic force microscopy to atomically resolve individual molecules from Murchison meteorite samples. They also proposed a method for extracting and preparing meteorite samples for investigation. By processing the samples, they were able to increase the fraction of molecules that could be resolved by atomic force microscopy and identify organic constituents and molecular moieties.
METEORITICS & PLANETARY SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Tao Wang, Sofia Sanz, Jesus Castro-Esteban, James Lawrence, Alejandro Berdonces-Layunta, Mohammed S. G. Mohammed, Manuel Vilas-Varela, Martina Corso, Diego Pena, Thomas Frederiksen, Dimas G. de Oteyza
Summary: This study characterized the magnetic states of chiral graphene nanoribbons by substitution of hydrogen atoms with ketones, leading to the generation of unpaired pi radicals that can interact via exchange coupling. The interactions between these radical states were found to depend significantly on factors such as chirality and the presence of ketone functionalization, and the parameters for accurately describing these systems within the mean-field Hubbard model were determined. Overall, this research provides insights for theoretically modeling and designing GNR-based nanostructures with tunable magnetic properties.
Article
Chemistry, Multidisciplinary
Maria Tenorio, Cesar Moreno, Pol Febrer, Jesus Castro-Esteban, Pablo Ordejon, Diego Pena, Miguel Pruneda, Aitor Mugarza
Summary: A synthetic strategy to fabricate nanometer scale, coherent lateral superlattice heterojunctions with atomically sharp band discontinuity is reported. By merging interdigitated arrays of different types of graphene nanoribbons, superlattices with chemical heterogeneity and nanoporous structures are obtained.
ADVANCED MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Rafal Zuzak, Jesus Castro-Esteban, Mads Engelund, Dolores Perez, Diego Pena, Szymon Godlewski
Summary: The formation of two types of nanographenes from custom-designed and synthesized molecular precursors has been achieved through intramolecular cyclodehydrogenation reactions on the TiO2 surface. Confirmation was made through spectroscopy measurements and theoretical modeling. Additionally, archetypic 7-armchair graphene nanoribbons have also been fabricated on the titanium dioxide surface through successive polymerization and cyclodehydrogenation reactions. These processes provide new perspectives for the rational design and synthesis of molecular nanostructures on semiconductors.
Article
Chemistry, Physical
Jan Patrick Calupitan, Tao Wang, Alejandro Perez Paz, Berta Alvarez, Alejandro Berdonces-Layunta, Paula Angulo-Portugal, Rodrigo Castrillo-Bodero, Frederik Schiller, Diego Pena, Martina Corso, Dolores Perez, Dimas G. de Oteyza
Summary: This paper reports the activation of a C-C sigma bond at room temperature on Cu(111). A biphenylene derivative's C-C sigma bond is broken, followed by the insertion of Cu from the substrate. The study offers new synthetic routes that can be used for in situ generation of activated species for the on-surface synthesis of novel C-based nanostructures. Overall significance of the article is rated 7.5 out of 10.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Roeland Vanhoutte, Marta Barniol-Xicota, Winston Chiu, Laura Vangeel, Dirk Jochmans, Steven De Jonghe, Hadeer Zidane, Haim M. Barr, Nir London, Johan Neyts, Steven H. L. Verhelst
Summary: The vulnerability of the modern society has been exposed by the COVID-19 pandemic, and it is crucial to have effective treatment options for infected individuals. We have designed a solid-phase synthesis route to create azapeptide activity-based probes for the SARS-CoV-2 main protease, which have shown to be potent inhibitors. These probes can be used to visualize the activity of the protease and the engagement of drugs in infected cells.
Article
Biochemistry & Molecular Biology
Jan Pascal Kahler, Vincenzo Davide Aloi, Julia Miedes Aliaga, Sara Kerselaers, Thomas Voets, Joris Vriens, Steven H. L. Verhelst, Marta Barniol-Xicota
Summary: TRPM3 is an ion channel expressed in nociceptive neurons and involved in pain perception. The antifungal compound clotrimazole (Clt) enhances TRPM3-induced pain by augmenting Ca(2+) signaling and opening a non-canonical pore. This study synthesized and evaluated Clt analogues to gain insights into their structure-activity relationship, identifying a pentafluoro-trityl analogue that acts as a TRPM3 agonist in the absence of the endogenous TRPM3 ligand.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Cesar Moreno, Xabier Diaz de Cerio, Manuel Vilas-Varela, Maria Tenorio, Ane Sarasola, Mads Brandbyge, Diego Pena, Aran Garcia-Lekue, Aitor Mugarza
Summary: Recent advances in surface-assisted synthesis have demonstrated the ability to create highly anisotropic nanoporous graphene structures by laterally coupling arrays of nanometer wide graphene nanoribbons. In this study, a new nanoporous graphene structure was synthesized in which the interribbon electronic coupling can be controlled by phenylene bridges. The versatility of this structure arises from the multiple configurations of phenylene cross-coupling and the twist angle, which can be altered by interaction with the substrate and other external stimuli.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Meijian Zhang, Andrea Bagan, Donna Martinez, Emma Barroso, Xavier Palomer, Santiago Vazquez, Carmen Escolano, Manuel Vazquez-Carrera
Summary: A novel series of AMPK activators were designed, synthesized, and evaluated in vitro to upregulate GDF15 levels as a strategy for treating obesity and type 2 diabetes mellitus. Compound 21 showed a higher increase in GDF15 mRNA levels and protein levels compared with metformin and BC1618 in human hepatic cells.
Article
Chemistry, Physical
Maria Tenorio, Cesar Moreno, Manuel Vilas-Varela, Jesus Castro-Esteban, Pol Febrer, Miguel Pruneda, Diego Pena, Aitor Mugarza
Summary: This article investigates the stability of pyridine and pyrimidine moieties in the process of synthesizing graphene nanoribbons and analyzes their structural and electronic properties through experiments and calculations. The results demonstrate that specific N-heterocycles can be preserved throughout the entire reaction steps by lowering the reaction temperature.
Article
Chemistry, Multidisciplinary
Cesar Moreno, Xabier Diaz de Cerio, Manuel Vilas-Varela, Maria Tenorio, Ane Sarasola, Mads Brandbyge, Diego Pena, Aran Garcia-Lekue, Aitor Mugarza
Summary: Recent advances in surface-assisted synthesis have shown that graphene nanoribbons can be coupled laterally to form nanoporous graphene structures. This graphene nanoarchitecture consists of weakly coupled semiconducting nanochannels with electron propagation characterized by interchannel quantum interferences. By utilizing phenylene bridges, the electronic coupling between the nanoribbons in the nanoporous graphene structure can be controlled, providing versatility through different phenylene cross-coupling configurations and twist angles. Simulation results demonstrate the ability to switch on/off or modulate the interribbon coupling using the chemical or conformational knob. Molecular bridges offer efficient tools for engineering quantum transport and anisotropy in carbon-based 2D nanoarchitectures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Medicinal
Sandra Codony, Jose M. Entrena, Carla Calvo-Tusell, Beatrice Jora, Rafael Gonzalez-Cano, Silvia Osuna, Ruben Corpas, Christophe Morisseau, Belen Perez, Marta Barniol-Xicota, Christian Grinan-Ferre, Concepcion Perez, Maria Isabel Rodriguez-Franco, Anton L. Martinez, M. Isabel Loza, Merce Pallas, Steven H. L. Verhelst, Coral Sanfeliu, Ferran Feixas, Bruce D. Hammock, Jose Brea, Enrique J. Cobos, Santiago Vazquez
Summary: A new benzohomoadamantane-based sEH inhibitor has been developed to improve the drug metabolism and pharmacokinetics properties for pain-related disorders, showing anti-allodynic and analgesic effects in murine models of capsaicin-induced allodynia and cyclophosphamide-induced cystitis.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Amelia Dominguez-Celorrio, Carlos Garcia-Fernandez, Sabela Quiroga, Peter Koval, Veronique Langlais, Diego Pena, Daniel Sanchez-Portal, David Serrate, Jorge Lobo-Checa
Summary: This study focuses on the on-surface synthesis of optically active manganese-phthalocyanine derivatives and investigates their isomeric configuration and reversible switching ability. The findings provide a feasible pathway towards the fabrication of magneto-optical transducers.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
