Article
Chemistry, Multidisciplinary
Matthew J. J. Genzink, Matthew D. D. Rossler, Herman Recendiz, Tehshik P. P. Yoon
Summary: Chiral acid catalysts are shown to promote highly selective visible-light photocycloadditions, leading to the synthesis of truxinate natural products. This general approach allows for the efficient synthesis of dimeric and pseudodimeric cyclobutane natural products with excellent enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Hoimin Jung, Mannkyu Hong, Marianna Marchini, Marco Villa, Philipp S. Steinlandt, Xiaoqiang Huang, Marcel Hemming, Eric Meggers, Paola Ceroni, Jiyong Park, Mu-Hyun Baik
Summary: The mechanism of [2 + 2] cycloadditions activated by visible light and catalyzed by bis-cyclometalated Rh(iii) and Ir(iii) photocatalysts was investigated. Experimental observations show that the Rh-based photocatalyst produces excellent yield and enantioselectivity, whereas the Ir-photocatalyst yields racemates. Two different mechanistic features were found to compete with each other.
Article
Chemistry, Physical
Joshua Clarke, Youngran Seo, Michel R. Gagne, Trandon A. Bender
Summary: This perspective discusses the key lessons learned from a program aiming to selectively deoxygenate cellulose-derived carbohydrates, with a focus on noneliminative mechanisms and the use of fluoroaryl borane catalysts. The control of substrate and catalyst over the deoxygenation process is crucial, and the lessons from this catalysis program can be applied to other important problems in catalysis and selectivity.
Article
Chemistry, Multidisciplinary
Yating Dai, Shuangshuang Liang, Guangkuo Zeng, Hongchun Huang, Xiaowei Zhao, Shanshan Cao, Zhiyong Jiang
Summary: This article presents a novel protocol based on chiral hydrogen-bonding catalytic strategy for converting electron-rich olefins to acceptors, and successfully carries out asymmetric photocycloadditions. The method is effective for electron-neutral olefins and allows the construction of all-carbon quaternary stereocentres with structurally similar aryl substituents.
Article
Chemistry, Physical
Christopher C. McAtee, Daniel J. Nasrallah, Ho Ryu, Michael R. Gatazka, Rory C. McAtee, Mu-Hyun Baik, Corinna S. Schindler
Summary: We describe a regioselective Lewis-acid-catalyzed method for the synthesis of highly functionalized cyclopentadienes incorporating diverse subunits. Insightful studies suggest that the mechanism involves Lewis-acid-catalyzed cycloadditions followed by stepwise oxetane fragmentation, resulting in the formation of functionalized cyclopentadienes. This work provides new insights into the design of catalytic carbonyl-olefin metathesis reactions.
Article
Chemistry, Multidisciplinary
Lydia Cox, Yuxiang Zhu, Philip J. Smith, Kirsten E. Christensen, Mireia Sidera Portela, Timothy J. Donohoe
Summary: A Ti(Oi-Pr)(4)-promoted 5- or 6-endo-trig cyclization for the synthesis of nitrogen heterocycles is presented. The use of HFIP as a key solvent enables the stereoselective formation of di- and tri-substituted pyrrolidines and piperidines while simultaneously forming a new C-C bond. The process involves the generation of a cationic intermediate from an allylic or benzylic alcohol and leads to the simultaneous generation of both a C-C and a C-N bond in a single step. Notably, different substituents on a nucleophilic amine yield either 2,3-trans- or 2,3-cis-substituted heterocycles. Lastly, enantiopure products can be obtained by using readily available enantiopure acyclic starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ana M. Martinez-Gualda, Pablo Domingo-Legarda, Thomas Rigotti, Sergio Diaz-Tendero, Alberto Fraile, Jose Aleman
Summary: The asymmetric synthesis of chiral polycyclic ethers is achieved through an intramolecular [2+2] photocycloaddition, utilizing a photocatalytically active iminium ion-based charge transfer complex under visible light irradiation. This method enables stereocontrolled [2+2] photocycloaddition, yielding tricyclic products with good enantiomeric ratios.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Lucas K. Johnson, Griffin L. Barnes, Sebastian A. Fernandez, Christopher D. Vanderwal
Summary: A radical/polar crossover annulation between allyl-substituted arenes and electron-deficient alkenes is reported. This reaction generates functionalized tetralin products via Co-catalyzed hydrogen atom transfer (HAT), avoiding hydrofluorination, hydroalkoxylation, hydrogenation, alkene isomerization, and radical polymerization reactions. The mild reaction conditions tolerate various functional groups, exhibiting broad substrate scope and enabling the rapid assembly of complex tetralins, which are difficult to access through traditional Diels-Alder cycloadditions of styrenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Pierre de Fremont, Nicolas Adet, Jordan Parmentier, Xuejuan Xu, Beatrice Jacques, Samuel Dagorne
Summary: This review comprehensively summarizes the synthesis, structure, and catalytic applications of group 12 metal (Zn, Cd, Hg) organocations reported since 2010. With appropriate ligand design and straightforward synthetic methodologies, various classes of stable and tunable Zn-II cationic complexes have been developed as potentially potent Lewis acids with catalytic activity. These recently developed Zn-II organocations have been extensively used as catalysts for important catalytic processes such as hydro-elementation and C-H functionalization of unsaturated small molecules. However, research contributions on Cd-II and Hg-II organocations are currently limited due to their toxicity.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Hiroyuki Miyamura, Shu Kobayashi
Summary: This paper describes the development of cooperative and synergistic catalyst systems of heterogeneous Rh-Pt bimetallic nanoparticle catalysts, Rh-Pt/DMPSi-Al2O3, and Sc(OTf)(3) in the liquid phase for the hydrogenation of arenes under very mild conditions. The cooperative activation achieved significant rate acceleration and successful hydrogenation of challenging substrates with strong electron-donating groups and sterically hindered substituents was demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Francisco de Azambuja, Jille Lenie, Tatjana N. Parac-Vogt
Summary: Inorganic clusters, specifically polyoxometalates (POMs), can serve as effective ligands for Hf(IV) Lewis acid metals in homogeneous metal catalysis. The interplay between the dielectric constant of the medium and the ligand structure is crucial for optimizing catalytic activity and promoting efficient amide bond formation. Changes in the dielectric constant can significantly impact the performance of the catalyst, highlighting the importance of understanding the relationship between medium properties and catalyst reactivity.
Article
Chemistry, Multidisciplinary
Wen-Xuan Cao, Lei Zhu, Yiyi He, Run Wang, Ming Liu, Qin Ouyang, Qing Xiao
Summary: The first aryne insertions into the carbon-iodine bond of heteroaryl iodides have been achieved. This novel reaction provides an efficient pathway for the synthesis of valuable building blocks 2-iodoheterobiaryls with excellent regioselectivity by reacting heteroaryl iodides and o-silylaryl triflates. The copper(I) catalyst, which contains a N-heterocyclic carbene (NHC) ligand, is essential for the reaction. Control reactions and DFT calculations suggest that the coordination of copper, acting as a Lewis acid, with nitrogen atoms of heteroaryl iodides mediates the aryne insertions into heteroaryl carbon-iodine bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Qinyi Li, Xinmin Liu, Weiyu Shi
Summary: This study confirms that the strong electric field and orbital asymmetric hybridization at charged clay surface substantially enhance Lewis acid-base reactions between Cu2+, Ca2+, Mg2+ and surface O. Infrared spectral analyses reveal changes in reaction intensity, highlighting the significance of these factors in clay catalyst design.
APPLIED SURFACE SCIENCE
(2022)
Article
Multidisciplinary Sciences
Haofu Zhu, Pan-Pan Zhou, Yao Wang
Summary: This study reports a new method for activating aziridines by cooperative sulfur-arsenic bonding interactions, enabling their use in cycloaddition reactions with nonactivated alkenes.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Fatima Almetwali, Jacques Rouden, Jerome Blanchet
Summary: This study developed novel boronic acids for catalyzed amide synthesis. The Lewis acidity of the boronic acids was estimated using computational techniques, and the increase in catalytic activity was confirmed with kinetic data. A set of newly developed catalysts were found, which showed superior efficacy in the coupling reaction of acids and amines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Rinat F. Salikov, Konstantin P. Trainov, Dmitry N. Platonov, Dmitry A. Davydov, Sangjun Lee, Igor S. Gerasimov, Michael G. Medvedev, Anastasia A. Levina, Aleksandr Yu Belyy, Yury Tomilov
Article
Chemistry, Multidisciplinary
Irina K. Goncharova, Kseniia P. Silaeva, Ashot V. Arzumanyan, Anton A. Anisimov, Sergey A. Milenin, Roman A. Novikov, Pavel N. Solyev, Yaroslav V. Tkachev, Alexander D. Volodin, Alexander A. Korlyukov, Aziz M. Muzafarov
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Alexander Yu. Belyy, Anastasia A. Levina, Dmitry N. Platonov, Rinat F. Salikov, Michael G. Medvedev, Yury V. Tomilov
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Denis D. Borisov, Grigory R. Chermashentsev, Roman A. Novikov, Yury Tomilov
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Maria A. Zotova, Roman A. Novikov, Alexander D. Volodin, Alexander A. Korlyukov, Yaroslav V. Tkachev, Victor A. Korolev, Yury V. Tomilov
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Polymer Science
K. Boldyrev, E. Tatarinova, I Meshkov, N. Vasilenko, M. Buzin, R. Novikov, V. Vasil'ev, E. Shtykova, L. Feigin, A. Bystrova, S. Chvalun, A. Muzafarov
Article
Chemistry, Multidisciplinary
Dmitry A. Denisov, Denis D. Borisov, Konstantin V. Potapov, Roman A. Novikov, Yury V. Tomilov
MENDELEEV COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
I. A. Borisova, A. V. Tarasova, K. V. Potapov, R. A. Novikov, Yu. V. Tomilov
RUSSIAN CHEMICAL BULLETIN
(2019)
Article
Biochemistry & Molecular Biology
Alexandra S. Latysheva, Vladimir A. Zolottsev, Alexander V. Veselovsky, Kirill A. Scherbakov, Galina E. Morozevich, Vadim S. Pokrovsky, Roman A. Novikov, Vladimir P. Timofeev, Yaroslav Tkachev, Alexander Y. Misharin
Article
Biochemistry & Molecular Biology
Anastasia A. Novoseltseva, Nikita M. Ivanov, Roman A. Novikov, Yaroslav V. Tkachev, Dmitry A. Bunin, Alexandra S. Gambaryan, Vadim N. Tashlitsky, Alexander M. Arutyunyan, Alexey M. Kopylov, Elena G. Zavyalova
Article
Chemistry, Inorganic & Nuclear
Roman A. Novikov, Anastasia A. Levina, Denis D. Borisov, Alexander D. Volodin, Alexander A. Korlyukov, Yaroslav Tkachev, Yana B. Platonova, Larisa G. Tomilova, Yury Tomilov
Article
Chemistry, Organic
Maria A. Belaya, Daniil A. Knyazev, Roman A. Novikov, Yury Tomilov
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Ivan A. Yaremenko, Yulia Yu Belyakova, Peter S. Radulov, Roman A. Novikov, Michael G. Medvedev, Nikolai Krivoshchapov, Alexander A. Korlyukov, Igor Alabugin, Alexander O. Terent'ev
Summary: Stable bridged azaozonides can be selectively assembled through a catalyst-free three-component condensation, showing thermal stability and unique chemical properties. Their chemical stability allows for selective transformations, including novel rearrangement reactions, due to the specific properties of the amino group in aminoperoxides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Pavel N. Solyev, Daria K. Sherman, Roman A. Novikov, Eugenia A. Levina, Sergey N. Kochetkov
Meeting Abstract
Biochemistry & Molecular Biology
A. Tyurin, V. Alferova, M. Shuvalov, R. Novikov
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)