Article
Chemistry, Multidisciplinary
Jeremy T. Maddigan-Wyatt, Mitchell T. Blyth, Jhi Ametovski, Michelle L. Coote, Joel F. Hooper, David W. Lupton
Summary: A phosphine-catalyzed approach to pyrrolines has been developed, involving two mechanistically unlinked catalytic processes, and successfully synthesizing various pyrrolines. The reaction shows high sensitivity to the selection of catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Marc Strohmann, Andreas J. Vorholt, Walter Leitner
Summary: This study presents a method for transforming olefins into branched amines by combining hydroformylation/aldol condensation tandem reaction with reductive amination. The method utilizes a combined multiphase system that can be recycled 9 times. The study demonstrates the feasibility of the method and its potential applications in the production of surfactants.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Jeanne Masson-Makdissi, Justin Ching, Cian M. Reid, Mark Lautens
Summary: A dual metal approach enables the use of unsymmetrical diallyl carbonates as viable enolate precursors for allylic alkylation reactions, allowing facile access to various alpha-quaternary allylated aldehydes and ketones. This methodology involves regioselective Pd-catalyzed decarboxylative oxidative addition and Rh-catalyzed isomerization.
Article
Chemistry, Physical
Didier Astruc, Guy Bertrand, Mohamed Eddaoudi, Yu Han, Kuo-Wei Huang, Johannes Lercher, Catherine Santini, Kazuhiro Takanabe, Mostafa Taoufik, Luigi Cavallo
Summary: This article discusses the contributions of Jean-Marie Basset in the field of catalysis. He introduced the approach of molecular organometallic chemistry to the study of supported catalysts, established the field of surface organometallic chemistry, and significantly improved numerous known reactions while also discovering new ones.
Article
Chemistry, Multidisciplinary
Xiaohua Hou, Xiaojian Chen, Xiang Gao, Lei Xu, Hui Zou, Li Zhou, Zong-Quan Wu
Summary: The binuclear vanadium alkylidene showed higher activity in ROMP of norbornene, leading to the formation of cyclic polymers. The size of the polymer ring could be adjusted by the vanadium catalyst structure and polymerization temperature. Similar results were also observed in the ROMP of cyclopentene.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Sarah E. Jenny, Juan M. Serviano, Ainara Nova, Graham E. Dobereiner
Summary: This study proposes a reaction pathway for a precatalyst that exhibits high Z selectivity in alkene isomerization. Computational modeling suggests that the isomerization occurs through an allyl hydride shift mechanism, where hydride migration from one position to another takes place. This is the first study to propose such a hydride migration mechanism in alkene isomerization.
Article
Chemistry, Physical
Jesus A. Avendano-Villarreal, Fabio G. Delolo, Artur V. Granato, Elena V. Gusevskaya, Eduardo N. dos Santos
Summary: A new and efficient method was developed to transform naturally occurring 1-propenylbenzenes into 2-arylpropylamines. This method involved a one-pot ethenolysis/hydroaminomethylation reaction and required careful selection of reaction conditions to achieve high yields. By adjusting the molar ratio of the catalysts, the interference between ethenolysis and hydroaminomethylation catalysts was avoided, resulting in the synthesis of nine 2-arylpropylamines with yields ranging from 75-93%.
Article
Chemistry, Multidisciplinary
Jie Wang, Xiaotian Qi, Xiao-Long Min, Wenbin Yi, Peng Liu, Ying He
Summary: This study presents a novel approach for the synthesis of axially chiral styrenes through tandem iridium catalysis. The method allows for efficient and selective preparation of chiral ligands needed for asymmetric synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Callum R. Woof, Derek J. Durand, Natalie Fey, Emma Richards, Ruth L. Webster
Summary: The catalytic mechanism of iron-catalyzed alkene isomerization reaction was studied through a combination of experimental and theoretical approaches. The results suggest that the isomerization of alkenes can be achieved through the combination of a hydride source and an iron(II) beta-diketiminate pre-catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biotechnology & Applied Microbiology
Grigorios Dedes, Anthi Karnaouri, Asimina A. Marianou, Konstantinos G. Kalogiannis, Chrysoula M. Michailof, Angelos A. Lappas, Evangelos Topakas
Summary: This study optimized the production of fructose from beechwood biomass hydrolysate and the subsequent conversion to HMF using homogeneous catalysis. The results showed that formic acid catalyst was the most effective for the dehydration of fructose to HMF, achieving high sugar conversion rates and HMF yields.
BIOTECHNOLOGY FOR BIOFUELS
(2021)
Article
Chemistry, Multidisciplinary
Arnab K. Maity, Annah E. Kalb, Matthias Zeller, Christopher Uyeda
Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Antonio Del Vecchio, Harry R. Smallman, Jennifer Morvan, Tom McBride, Duncan L. Browne, Marc Mauduit
Summary: This article introduces the versatility of olefin metathesis and its successful applications in natural product synthesis and the valorization of renewable feedstocks. In addition, flow chemistry has gained significant interest as a valuable alternative to traditional batch chemistry and has paved the way for new transformations. The article highlights the promising application of continuous-flow methods in olefin metathesis, addressing typical issues such as undesired self-reactions and ethylene-mediated catalyst deactivation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Saptashwa Chakraborty, Bijoyananda Mishra, Pratim Kumar Das, Sandip Pasari, Srinivas Hotha
Summary: The silver-assisted gold-catalyzed activation of alkynyl glycosyl carbonate donors is a versatile approach for the synthesis of various types of N-glycosides, including purine and pyrimidine nucleosides, asparagine glycosides, and quinolin-2-one N-glycosides. This method enables the synthesis of nucleosides that are difficult to obtain through other means. Additionally, it can be used to easily synthesize 2'-modified nucleosides and dipeptide disaccharide units of chloroviruses.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Kevin Schlenker, Elizabeth G. Christensen, Asylbek A. Zhanserkeev, Gabriel R. McDonald, Emily L. Yang, Kevin T. Lutz, Ryan P. Steele, Ryan T. VanderLinden, Caroline T. Saouma
Summary: The study reveals that substrate binding to the backbone of the catalyst is advantageous for the hydrogenation of CO2, contrary to previous assumptions. The enhanced hydricity observed upon deprotonation may have broad applicability to systems capable of undergoing metal-ligand cooperativity. This work demonstrates the use of thermochemical analysis to advance mechanistic understanding in (de)hydrogenation catalysis.
Article
Chemistry, Multidisciplinary
Dmitry S. Belov, Gabriela Tejeda, Charlene Tsay, Konstantin V. Bukhryakov
Summary: Vanadium-based catalysts have been demonstrated to catalyze ring-closing olefin metathesis reactions by well-defined V chloride alkylidene phosphine complexes, exhibiting good functional group tolerance. The properties of the imido group and phosphine were found to play a crucial role in the stability of active intermediates.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Zhiyong Hu, Xiao-Jing Wei, Jens Handelmann, Ann-Katrin Seitz, Ilja Rodstein, Viktoria H. Gessner, Lukas J. Goossen
Summary: By tailoring ylide-functionalized phosphines to fit the requirements of Negishi couplings, the challenges in Ar-H coupling have been overcome and the substrate scope has been expanded. Record-setting activities were achieved in arylations using a cyclohexyl-YPhos ligand, enabling couplings of aryl chlorides with Reformatsky reagents and the synthesis of diversely functionalized arylacetic and arylpropionic acid derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Emiliano Feresin, Mykhailo Kondratiuk, Julia Nowack, Lukas J. Goossen
Summary: Citizens can adopt behavioral precautions such as practicing good hand hygiene and using disinfectants to prevent the spread of the SARS-CoV-2 virus. The role of water as a solvent in hand washing and sanitizing processes is essential for breaking down the virus membrane with soap molecules and facilitating the virus inactivation with alcohol.
CHEMIE IN UNSERER ZEIT
(2021)
Review
Chemistry, Organic
Jonas F. Goebel, Zhongyi Zeng, Lukas J. Goossen
Summary: The article summarizes recent advances in the synthesis of biaryls through electrooxidative processes, with a particular focus on electrooxidative C-H/C-M couplings and dehydrogenative couplings.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Nardana Sivendran, Florian Belitz, Daniel Sowa Prendes, Angel Manu Martinez, Rochus Schmid, Lukas J. Goossen
Summary: This study explores the application of Trihalide salts in photochemical dediazotizing halogenations, revealing that high yields and outstanding selectivities for halogenation can be achieved without the need for metal catalysts. In addition, convenient protocols are disclosed for the brominations, iodinations, and chlorinations of diverse functionalized derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Xiao-Jing Wei, Bingxiang Xue, Jens Handelmann, Zhiyong Hu, Heidar Darmandeh, Viktoria H. Gessner, Lukas J. Goossen
Summary: In this study, a novel catalyst prYPhos was developed to promote Pd-catalyzed Suzuki-Miyaura couplings. Under mild reaction conditions, this catalyst efficiently produced various (hetero)biaryls with good tolerance towards sensitive functional groups and steric hindrance. The results demonstrated that this catalyst exhibited high selectivity in selectively coupling chlorides and leaving triflate groups intact.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Ann-Katrin Seitz, Philipp J. Kohlpaintner, Tim Lingen, Marco Dyga, Fiona Sprang, Michael Zirbes, Siegfried R. Waldvogel, Lukas J. Goossen
Summary: Concentrated peroxodicarbonate solutions have been successfully prepared through electrolysis of carbonate solutions, and their synthetic potential has been demonstrated in various transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Florian Belitz, Ann-Katrin Seitz, Jonas F. Goebel, Zhiyong Hu, Lukas J. Goossen
Summary: In the presence of a [Ru(p-cymene)Cl-2](2)/triethylphosphine/lithium carbonate catalyst system, aryl bromides undergo (Z)-selective couplings with unprotected 2-arylacrylic acids to form (Z)-diarylacrylic acids. This vinylic C-H functionalization proceeds with high yields and (Z/E)-ratios, and it can tolerate a wide range of functional groups. Mechanistic studies indicate that the vinylic C-H activation proceeds via base-assisted cyclometalation and it shows orthogonal stereoselectivity.
Article
Chemistry, Organic
Ann-Katrin Seitz, Tim van Lingen, Marco Dyga, Philipp J. Kohlpaintner, Siegfried R. Waldvogel, Lukas J. Goossen
Summary: The N-oxidation of tertiary amines can be achieved using electrochemically generated peroxodicarbonate solutions. The presence of EDTA and 2,2,2-trifluoroacetophenone as mediators is crucial for converting water-insoluble substrates.
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
Jonas F. Goebel, Julian Loeffler, Zhongyi Zeng, Jens Handelmann, Albert Hermann, Ilja Rodstein, Tobias Gensch, Viktoria H. Gessner, Lukas J. Goossen
Summary: Palladium-catalyzed couplings of silicon enolates with aryl electrophiles are limited to expensive bromide substrates. However, a study using ylide functionalized phosphines (YPhos) showed promising results in coupling inexpensive aryl chlorides with alpha-trimethylsilyl alkylnitriles. A statistical model was developed to predict catalyst structures with superior performance, leading to the synthesis of pharmaceutically significant compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jonas F. Goebel, Johanna Stemmer, Florian Belitz, Lukas J. Goossen
Summary: The 3d-metal catalyst Mn(CO)(5)Br efficiently promotes ortho C-H allylations of arenecarboxylates in the presence of neocuproine as the ligand. The selectivity of this relatively simple directing group and catalyst system surpasses the state-of-the-art, exclusively producing mono-allylated products with high selectivities for the least hindered ortho-position. The directing group can be selectively removed by in situ decarboxylation, providing a regioselective access to allyl arenes. The preparative utility of this process and its orthogonality to other approaches were demonstrated by the synthesis of 44 products with otherwise difficult substitution patterns.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tim van Lingen, Valentina Bragoni, Marco Dyga, Benjamin Exner, Daniel Schick, Christoph Held, Gabriele Sadowski, Lukas J. Goossen
Summary: This study addresses the challenge of salt waste formation in C-H carboxylations, which hinders the use of CO2 as a C-1 building block in industrial synthesis. Through a circular process, dimethyl succinate, a C-4 base chemical, is produced from CO2 and acetylene. Increased CO2 pressure allows for reversible acidification and esterification of the succinate salt, while the cesium base and hydrogenation catalyst are regenerated for reuse. Thermodynamic modeling reveals the origins of the reversible acidity switch and the crucial roles of the cesium base and NMP/MeOH solvents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Philipp J. Kohlpaintner, Lucas Marquart, Lukas J. Goossen, Siegfried R. Waldvogel
Summary: Peroxodicarbonate is a green and underexplored oxidizer generated electrochemically from aqueous carbonate solutions. With advanced electrolyzer technology, highly concentrated solutions are now accessible. These solutions have been successfully used as green oxidizers in deborolative hydroxylations, leading to the synthesis of a variety of phenols and alcohols with yields up to 99% from organoboron compounds using environmentally friendly solvents. The scalability of this transformation to multi-gram batch sizes has also been demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Florian Papp, Daniel Sowa Prendes, Sourav Manna, Ann-Katrin Seitz, Sofiya Kostiukovska, Julian Loeffler, Viktoria H. Gessner, Lukas J. Goossen
Summary: Palladium complexes with ylide-functionalized phosphine ligands catalyze the arylation of N-protected hydantoins with aryl chlorides, enabling the synthesis of a wide variety of hydantoins, including derivatives of the anticonvulsant drugs phenytoin and mephenytoin. Selective monoarylations, sequential diarylations, and arylation-alkylation sequences have been achieved, along with stepwise deprotection strategies.
Article
Chemistry, Applied
Bingxiang Xue, Jie Shen, Sourav Manna, Angelino Doppiu, Lukas J. Goossen
Summary: A new catalyst has been discovered that can selectively introduce a primary amino group into aromatic compounds, and it can efficiently promote the amination reaction to synthesize primary anilines within 30 minutes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
