Article
Chemistry, Multidisciplinary
Ziyan Zhang, Nikita Kvasovs, Anastasiia Dubrovina, Vladimir Gevorgyan
Summary: This method utilizes visible light-induced and Bronsted acid-assisted generation of hybrid palladium C(sp(3))-centered radical intermediate, enabling efficient transformation of a wide range of vinyl arenes, heteroarenes, and diazo compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Danish Khan, Iram Parveen
Summary: A new family of phosphine-free Amino-chroman-4-one bidentate ligands were successfully synthesised and characterised, showing efficient catalytic activity in C-C bond formation. They demonstrated excellent performance in Suzuki-Miyaura and Mizoroki-Heck coupling reactions, with a broad range of substrates well tolerated under the optimized reaction conditions. Mass spectrometry was used to characterize the metal complex and intermediates formed in the catalytic cycle, supporting the reaction mechanism.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Zi-Sheng Chen, Xiao-Yan Huang, Qing Liu, De-Xin Song, Fang Yang, Kegong Ji
Summary: This article presents a synergistic Rh(II)/Pd(0) dual-catalyzed strategy for the three-component oxy-allylation of a-diazo esters, alcohols, and allylic benzoates. The reaction involves the trapping of active protic oxonium ylides with catalytic p-allyl Pd(II) intermediates. Interestingly, water also participates in the reaction through a different allylic migratory insertion of palladium-carbenes. These transformations offer a straightforward approach to various a-ternary allylated carboxylic esters using readily available starting materials under redox-neutral conditions, leading to the successive generation of two new C-O and C-C bonds at the carbene center. CO 2022 Elsevier Inc. All rights reserved.
JOURNAL OF CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Jia-Qi Xie, Ren-Xiao Liang, Yi-Xia Jia
Summary: This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, covering intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates, providing a clear structure for readers.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Xiao-Qing Han, Lei Wang, Ping Yang, Jing-Yuan Liu, Wei-Yan Xu, Chao Zheng, Ren-Xiao Liang, Shu-Li You, Junliang Zhang, Yi-Xia Jia
Summary: A palladium-catalyzed intramolecular enantioselective Mizoroki-Heck reaction of naphthalenes has been developed, leading to the formation of a series of unique heterocyclic compounds with enantiomeric excess values retained. The reaction relies on the use of a chiral sulfonamide phosphine ligand to inhibit competitive and undesired reactions.
Article
Chemistry, Multidisciplinary
Anna Domzalska-Pieczykolan, Ignacio Funes-Ardoiz, Bartlomiej Furman, Carsten Bolm
Summary: Efficient protocols for selective α- and β-arylations of structurally diverse vinyl ethers were developed, showing high economic benefits and reduced waste production. Computational studies provided insights into the key factors determining the regioselectivities of the reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Anna Domzalska-Pieczykolan, Ignacio Funes-Ardoiz, Bartlomiej Furman, Carsten Bolm
Summary: This study developed simple and efficient protocols for palladium-catalyzed regioselective alpha- and beta-arylations of structurally diverse vinyl ethers. The methods are applicable to a wide range of substrates and produce low waste due to the use of limited reagents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Subhankar Ghosh, Shital K. Chattopadhyay
Summary: In this study, a single metal catalyst and air as the oxidant were used to achieve tandem C-H arylation and C-H amidation of cis-cinnamyl hydroxamates, leading to the regioselective formation of a 3-aryl-2-quinolone ring system. Under identical conditions, the corresponding trans-isomer resulted in a 4-aryl-2-quinolone derivative. The observed complementary regioselectivity during the tandem C-H arylation and C-H amidation of isomeric substrates is unusual and has potential applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Inorganic & Nuclear
Mathews Alisha, Rose Mary Philip, Gopinathan Anilkumar
Summary: This article provides a comprehensive review of rhodium-catalysed Heck type reactions, including oxidative, decyanative, desulfitative, decarbonylative Heck reactions, and even Heck type cyclizations, covering literature until 2021.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Holly E. Bonfield, Damien Valette, David M. Lindsay, Marc Reid
Summary: This Minireview provides a timely summary of the development of palladium-catalyzed asymmetric redox-relay Heck-type processes, showcasing their importance in introducing remote stereocenters and applications in the pharmaceutical field. Additionally, a mechanistic summary, discussion on limitations, and outlook on future research directions are included to complement the overview.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Linhao Liu, Henri Doucet
Summary: A new method for functionalizing the beta-C-H bonds of thiophene compounds has been developed, achieving vinylation at the beta-position using Pd-catalysis. The synthetic route has good tolerance for various substituents and employs readily available and stable catalysts as well as inexpensive bases. This study provides an important methodological foundation for the synthesis of thiophene compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Hao Sun, Chenzhe Xu, Xiaoting Yang, Lei Tao, Zheng Wang, Haitao Zhang, Xiang Ji, Juanjuan Ma, Lin Liu, Zhiwei Tong, Zhong Chen
Summary: A novel composite Pd@MgAl-LDH was prepared by using MgAl layered double hydroxide (LDH) as the host material and assembling the precursor (PdCl42-) with exfoliated LDH nanosheets followed by in-situ reduction. The heterogeneous catalyst exhibited evenly distributed Pd NPs with an average particle size of about 3.27 nm supported on LDH nanosheets. The Pd@MgAl-LDH catalyst showed excellent catalytic efficiency for the Heck reaction and could be reused 5 times without significant loss of catalytic activity.
APPLIED CLAY SCIENCE
(2023)
Article
Chemistry, Organic
Huahua Liu, Yuping Xiong, Zhiyuan Chen
Summary: An efficient intramolecular Heck annulation reaction and trapping of the resulting cyclic alpha-oxindolylpalladium species by CO and NH-sulfoximine at room temperature has been demonstrated, providing excellent yields of 3,3-disubstituted beta-indoly sulfoximidoyl amides under very gentle reaction conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Fathima F. Pary, Ravi Teja Addanki Tirumala, Marimuthu Andiappan, Toby L. Nelson
Summary: Significant attention has been devoted to copper and copper oxide nanocatalysts in the past few decades, due to copper's natural abundance, low cost and lower toxicity. Cu2O nanoparticles exhibit versatility in catalyzing carbon-carbon and carbon-heteroatom bond-forming reactions. In this study, oxidative C-C homocoupling reactions were demonstrated using Cu2O nanoparticles, with the formation of homogeneous copper catalytic species through substrate-induced leaching.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Applied
Min Liu, Kelu Yan, Jiangwei Wen, Xue Li, Xiaoyu Wang, Fengjie Lu, Xiu Wang, Hua Wang
Summary: The rhodium(III)-catalyzed C-H/diazo coupling and tandem annulation of 3-oxopent-4-enenitriles have been proposed for the synthesis of polysubstituted phenols, yielding most products in good yields. Preliminary mechanistic studies and derivatization reactions of phenol products were also conducted, offering an alternative approach for synthesizing a variety of useful phenols.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Medicinal
Benson Oloya, Jane Namukobe, Matthias Heydenreich, Willy Ssengooba, Bernd Schmidt, Robert Byamukama
Summary: Lupeol, sesamin, trans-fagaramide, and other compounds isolated from the stem bark of Zanthoxylum leprieurii showed moderate to significant antimycobacterial activities, with trans-fagaramide potentially serving as a vital template for novel and effective tuberculosis drugs.
NATURAL PRODUCT COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Patrick Sand, Bernd Schmidt
Summary: Vinylsulfonamides do not react with acetanilides in Pd-catalyzed oxidative Heck-coupling reactions, but this limitation has been overcome by using a C-H-activation protocol based on Ru-Cu-Ag-catalysis. The Ru-Cu-Ag-catalyzed conditions are more reliable and reproducible compared to Pd-catalyzed C-H-activation. The resulting functionalized styrenyl sulfones and -sulfonamides can serve as starting materials for synthesizing sulfonyl pyrroles and sulfonyl pyrrolo[2,3-c]quinolines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kajsa Lood, Triin Tikk, Mandy Krueger, Bernd Schmidt
Summary: The cross-metathesis reactions of four combinations of type-I olefins isoeugenol and 4-hydroxy-3-methoxystyrene with type-II olefins acrolein and crotonaldehyde were investigated. Only the combination of isoeugenol and crotonaldehyde showed useful conversions. The high reactivity of this combination was demonstrated by the synthesis of 7-methoxywutaifuranal with a 44% yield. Methylene capping was suggested as the reason for the superior performance of crotonaldehyde in these reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Yuhang Zhao, Radwan M. Sarhan, Alberto Eljarrat, Zdravko Kochovski, Christoph Koch, Bernd Schmidt, Wouter Koopman, Yan Lu
Summary: Bimetallic nanostructures can generate a new type of photo-enhanced nanoreactors by utilizing photo-generated heat to accelerate catalytic reactions. The study demonstrates that the photothermal conversion of Au-Pd nanorods can be improved by coating with polydopamine or TiO2, resulting in increased reaction rates.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Applied
Gaston Bravo-Arrepol, Jose Becerra, Leandro Ortiz, Jaime Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Alexandra Kelling, Eric Sperlich, Tomasz M. Karpinski, Cristian Paz
Summary: Furofuran lignanes, which are obtained from various plants, possess important biological activities for treating infectious diseases, inflammatory diseases, and metabolic disorders. In this study, eudesmin, a furofuran lignan, was easily isolated from Araucaria araucana knots using soxhlet extraction and cryo-crystallization. The bromination of eudesmin led to the formation of epieudesmin and its corresponding mono and di-brominated derivatives. The structures of these compounds were determined by NMR and X-ray diffraction. Furthermore, eudesmin exhibited moderate activity against Candida yeast strains, while epieudesmin and the bromine derivatives showed no activity.
NATURAL PRODUCT RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Nicole Cortez, Victor Marin, Veronica A. Jimenez, Victor Silva, Oscar Leyton, Jaime R. Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Viviana Burgos, Paola Duran, Cristian Paz
Summary: Fungal biotransformation is an effective and attractive method for synthesizing specific compounds with unique chemical functionality. In this study, Cladosporium antarcticum was used to produce novel drimane sesquiterpenoid alcohols with activity against Candida yeast. The compounds were obtained through high-yield reduction of polygodial and isotadeonal. The antifungal activity of the compounds was evaluated, and it was found that one of the compounds showed potent inhibitory effects against three Candida species.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Victor Marin, Bryan Bart, Nicole Cortez, Veronica A. Jimenez, Victor Silva, Oscar Leyton, Jaime R. Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Viviana Burgos, Cristian Paz
Summary: This study identified compounds from Drimys winteri (Winteraceae) that possess antifungal activity against Candida yeast. The most active compound, polygodial, showed fungistatic activity but caused irritation to the eyes and skin. A new compound, winterdial, was also discovered with potential antifungal properties. These findings are valuable for the development of more potent and safer drugs to treat candidiasis using natural compounds as a primary source.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Patrick Sand, Bernd Schmidt
Summary: The regioselectivity of two mechanistically distinct alkenylation reactions catalyzed by in situ-formed cationic transition metal complexes was studied using N-allyl-N-phenylethenesulfonamide as a model compound. Orthogonal selectivity was observed for the Ru-catalyzed C-H-activating alkenylation with acetanilides, which occurs preferentially at the electron deficient double bond, and for a Pd-catalyzed Heck-type coupling with arene diazonium salts, which occurs preferentially at the more electron rich double bond of the N-allyl substituent.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Plant Sciences
Vaderament-Alexe Nchiozem-Ngnitedem, Eric Sperlich, Valaire Yemene Matieta, Jenifer Reine Ngnouzouba Kuete, Victor Kuete, Ejlal A. A. Omer, Thomas Efferth, Bernd Schmidt
Summary: FicucariconeD and its 4'-demethyl congener 2 are isoflavones obtained from Ficus carica fruits with a 5,7-dimethoxy-6-prenyl-substituted A-ring. They were synthesized for the first time in six steps from 2,4,6-trihydroxyacetophenone. The compounds showed no cytotoxicity against leukemia cell lines but exhibited antimicrobial activities, especially when combined with the efflux pump inhibitor PA beta N.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Physical
Radwan M. M. Sarhan, Sergio Kogikoski Jr, Robin M. M. Schuermann, Yuhang Zhao, Andreas Krause, Bernd Schmidt, Ilko Bald, Yan Lu
Summary: This study presents a facile and environmentally friendly method to synthesize black gold nanoparticles via a one-step green synthesis at room temperature using commonly known precursors. The self-assembly of in situ-formed small nanoparticles followed by a fusion step creates extensive networks of nanowires, resulting in strong photothermal and surface-enhanced Raman scattering (SERS) effects. The black gold nanoparticles show potential for applications in solar energy conversion and photothermal therapy.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Plant Sciences
Benson Oloya, Jane Namukobe, Matthias Heydenreich, Willy Ssengooba, Johannes Martin, Heiko Michael Moeller, Bernd Schmidt, Robert Byamukama
Summary: Two new compounds with strong anti-mycobacterial activities were isolated from the root bark of Z. leprieurii, which could potentially serve as new and highly effective drugs for tuberculosis.
PHYTOCHEMISTRY LETTERS
(2023)
Article
Chemistry, Organic
George Kwesiga, Julia Greese, Alexandra Kelling, Eric Sperlich, Bernd Schmidt
Summary: Isoflavones were synthesized via Suzuki-Miyaura coupling using para-phenolboronic acid and para-methoxybenzene boronic acid as reactants. The optimized conditions led to higher yields of isoflavones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Rebeca Perez, Claudia Figueredo, Viviana Burgos, Jaime R. Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Andreas Koch, Jennifer R. Deuis, Irina Vetter, Cristian Paz
Summary: Maqui, a tree native to Chile, is used by the Mapuche people as an anti-inflammatory agent for the treatment of digestive ailments, fever, and skin lesions. Maqui fruits are considered a superfruit with potential health benefits, including antioxidant, cardioprotective, and anti-inflammatory properties. The leaves of maqui contain alkaloids, polyphenols, and terpenes. The alkaloids, aristoteline and hobartine, were found to inhibit Na(V)1.8, a key Na-V isoform involved in pain sensation, suggesting a potential mechanism for the reported analgesic properties of maqui.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Eric Sperlich, Alexandra Kelling, George Kwesiga, Bernd Schmidt
Summary: The molecular structures of three closely related isoflavones were determined and analyzed using X-ray diffraction and various analysis methods. The study found that non-covalent interactions play a crucial role in the formation of supramolecular structures and the macroscopic properties of the compounds.
Article
Chemistry, Organic
Andreas Krause, Eric Sperlich, Bernd Schmidt
Summary: Itaconic acid esters and hemiesters undergo efficient Pd-catalyzed coupling reactions with arene diazonium salts, leading to the synthesis of benzazepine-2-ones in one to two steps with high yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)