Article
Chemistry, Multidisciplinary
Dongxu Zuo, Qun Wang, Long Liu, Tianzeng Huang, Michal Szostak, Tieqiao Chen
Summary: The challenging transamidation of unactivated tertiary amides has been accomplished via cooperative acid/iodide catalysis. This method provides a direct route to amide-to-amide bond interconversion with excellent chemoselectivity using equivalent amounts of amines. The combination of acid and iodide activates the amide C-N bond through electrophilic catalytic activation, enabling the production of new desired transamidated products with wide substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiamin Wang, Sujuan Shuai, Lishe Gan, Yongxin Luo, Huimin Jin, Lingfeng Chen, Dong Zou, Guang Liang, Patrick J. Walsh, Jie Li
Summary: This study presents a highly chemoselective amidation method for the Boc and amide groups of N-R-N-Boc arylamides. The method is practical and easy to carry out, allowing for the preparation of N-aroylureas or imides in high yields without the use of transition metals. The choice of base determines the reactivity of the different carbonyl groups, with arylamides undergoing amidation with (KOBu)-Bu-t and imides being produced with LiOH. DFT studies are employed to investigate the mechanisms involved. These chemoselective methods are expected to be valuable in synthetic and medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shweta Singh, Jeyakumar Kandasamy
Summary: Acyl hydrazides can be synthesized from amides at room temperature through N-activation reactions. A wide range of functionalized primary and secondary amides were transformed into N-Boc, N-nitroso, and N-tosyl amides, which were then subjected to transamidation with hydrazine hydrate to yield the desired acyl hydrazides in yields of 76-94%. The developed methodology has the advantages of broad substrate scope, shorter reaction time, and mild reaction conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Danfeng Ye, Hao Chen, Zhiyuan Liu, Chuanhu Lei
Summary: The new protocol allows for the transamidation of N-benzyl-N-Boc-amides under transition metal-free and base-free conditions, resulting in a diverse array of substituted amides in good yields. Notably, the reaction preserves enantiopurity with respect to chiral amino-acid-derived nucleophiles. The method has been successfully applied in the synthesis of pro-drugs and the antidepressant moclobemide.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shweta Singh, Jeyakumar Kandasamy
Summary: A developed method for C-C coupling reactions allows a wide range of functionalized N-Cbz amides to react with enolizable esters, ketones, and amides to produce 1,3-dicarbonyl compounds under mild conditions. The reactions proceed at room temperature in the presence of LiHMDS in CPME, resulting in good to excellent yields of desired products in a short reaction time.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hai Lin, Shengzhang Liu, Qing Li, Qi Zhang, Lingyun Yang, Tao Wang, Jin Luo
Summary: This article describes a novel and efficient electrochemical oxidative transamidation of tertiary amines with N-acyl imides. The protocol is environmentally friendly and easy to handle, as tertiary amines are used as surrogates for secondary amines. The C-N bond of tertiary amines is cleaved, preparing amide compounds in a facile approach with 29 examples in yields ranging from 11% to 80%.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Andrey Shatskiy, Andrey A. Bardin, Michael Oschmann, Roc Matheu, Jordi Benet-Buchholz, Lars Eriksson, Markus D. Karkas, Eric Johnston, Carolina Gimbert-Surinach, Antoni Llobet, Bjorn Akermark
Article
Chemistry, Multidisciplinary
Michael Oschmann, Clotilde Placais, Anuja Nagendiran, Jan-E Backvall, Oscar Verho
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Alexander J. Schmitz, Alexander Ricke, Michael Oschmann, Oscar Verho
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Biochemistry & Molecular Biology
Michael Oschmann, Linus Johansson Holm, Monireh Pourghasemi-Lati, Oscar Verho
Article
Chemistry, Physical
Ning Yuan, Arnar Gudmundsson, Karl P. J. Gustafson, Michael Oschmann, Cheuk-Wai Tai, Ingmar Persson, Xiaodong Zou, Oscar Verho, Eva G. Bajnoczi, Jan-E Backvall
Summary: By utilizing in situ X-ray absorption spectroscopy (XAS), researchers uncovered the deactivation mechanism of palladium catalyst in the cycloisomerization of acetylenic acids and developed an improved catalytic protocol that is less prone to deactivation.
Review
Chemistry, Multidisciplinary
Biswanath Das, Ahibur Rahaman, Andrey Shatskiy, Oscar Verho, Markus D. Karkas, Bjorn Akermark
Summary: Research efforts have been focused on designing efficient catalysts for water oxidation, with a particular interest in ruthenium-based catalysts due to their robust nature and high activity. Strategic modifications of ligand structures to enable proton-coupled electron transfer (PCET) and atom proton transfer (APT) play a central role in improving the catalysts' performance for O-O bond formation during water oxidation. Introduction of carboxylate groups in the ligands has been shown to improve stability, prevent metal leaching, and enhance proton donor/acceptor properties, ultimately leading to improved efficiency and reduced overpotential in the water oxidation reaction.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Monireh Pourghasemi Lati, Jonas Stahle, Michael Meyer, Oscar Verho
Summary: This work describes a synthetic route to access chiral cyclobutane keto acids with two stereocenters from inexpensive terpene myrtenal. The developed route includes a key C(sp(2))-H arylation step and an ozonolysis-based ring-opening step, allowing incorporation of various groups and finding applications in the synthesis of natural product-like compounds and small molecule libraries.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Correction
Chemistry, Physical
Ning Yuan, Arnar Gudmundsson, Karl P. J. Gustafson, Michael Oschmann, Cheuk-Wai Tai, Ingmar Persson, Xiaodong Zou, Oscar Verho, Eprimeva G. Bajnoczi, Jan-E. Backvall
Article
Chemistry, Physical
Biswanath Das, Esteban Alejandro Toledo-Carrillo, Lin Li, Fei Ye, Jianhong Chen, Adam Slabon, Oscar Verho, Lars Eriksson, Mats Gothelid, Joydeep Dutta, Bjorn Akermark
Summary: The electrocatalytic activity of a cobalt-containing, water-soluble molecular water oxidation catalyst was reported, and its stability and activity were significantly enhanced by anchoring it onto modified carbon cloth.
Article
Chemistry, Multidisciplinary
Jianwei Zhang, Biswanath Das, Oscar Verho, Jan-E Backvall
Summary: Here we describe an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization reaction for the synthesis of gamma-lactones and spirolactones, exhibiting excellent chemoselectivity. Interestingly, electrocatalysis was found to enhance the reaction rate of the tandem process, leading to a more efficient reaction compared to chemical redox conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Biswanath Das, Esteban A. Toledo-Carrillo, Guoqi Li, Jonas Stahle, Thomas Thersleff, Jianhong Chen, Lin Li, Fei Ye, Adam Slabon, Mats Gothelid, Tsu-Chien Weng, Jodie A. Yuwono, Priyank V. Kumar, Oscar Verho, Markus D. Karkas, Joydeep Dutta, Bjorn Akermark
Summary: In this study, a bifunctional and electrochemically regenerable molecular electrode was successfully developed for the stable production of hydrogen. By anchoring a highly active ruthenium electrocatalyst onto modified fluorine-doped carbon cloth, the electrode exhibited high activity for both oxygen evolution reaction and hydrogen evolution reaction in acidic conditions. The electrode design showed excellent electrochemical regeneration performance after prolonged use.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Chemistry, Inorganic & Nuclear
Lin Li, Biswanath Das, Ahibur Rahaman, Andrey Shatskiy, Fei Ye, Peihong Cheng, Chunze Yuan, Zhiqi Yang, Oscar Verho, Markus D. Karkas, Joydeep Dutta, Tsu-Chien Weng, Bjorn Akermark
Summary: This study reports a new type of active anode based on a molecular catalyst for electrochemically-driven water oxidation. By attaching the catalyst to glassy carbon, the stability and reactivity of the anode are improved. Using various characterization techniques, it is demonstrated that this anode performs comparably to state-of-the-art metal oxide anodes.
DALTON TRANSACTIONS
(2022)
Meeting Abstract
Chemistry, Multidisciplinary
Oscar Verho, Monireh Pourghasemi-Lati, Michael Oschmann
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
