Article
Chemistry, Organic
Shuangrong Liu, Zhimin Ying, Qi Zhu, Xiuwen Zhong, Jie Cen, You Wu, Yongping Yu, Jiaan Shao, Wenteng Chen
Summary: This study reveals a step-economical nitrite-triggered cycloaddition reaction for the modular assembly of isoxazoles (or isoxazolines) from bromide and alkyne/alkene. The reaction offers high regio-selectivity, excellent efficiency, wide functionality tolerance, biocompatible conditions, and operational simplicity, making it suitable for the direct diversification of pharmaceuticals and bio-relevant motifs.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Radell Echemendia, Kleber T. de Oliveira, Antonio C. B. Burtoloso
Summary: A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides.
Article
Chemistry, Applied
Giorgiana Denisa Bisag, Silvia Ruggieri, Mariafrancesca Fochi, Luca Bernardi
Summary: Stabilised sulfur ylides reacted with salicylaldehydes under catalyst- and substrate-dependent conditions, forming either 2H-chromenes or dihydrobenzofurans. Unusual mechanisms were investigated, leading to the proposal of two unique reaction routes involving two ylide units. These pathways were validated by selective switches achieved through modifying the nucleophilicity of the sulfur ylide and adjusting the loading of the Bronsted acid catalyst.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Duo Fu, Jiaxi Xu
Summary: A Halide-promoted pyridinylation reaction between alpha-acyl sulfonylmethylides and 2-halo-1-methylpyridinium iodides in a transition-metal-free protocol is described. This method offers a facile and practical approach for constructing methylthio- and pyridinoxyl-substituted vinylsulfones. The reaction involves the formation of a C-O bond and consecutive breaking of C-S, C-Cl and C-N bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Fengkai Qiu, Zheng Wang, Dan Zhao, Linghui Zeng, Chong Zhang, Huajian Zhu, Jiankang Zhang, Jiaan Shao
Summary: The synthesis of 3-thioether-substituted dihydrofuro[2,3-b]benzofurans has been achieved through the [3 + 2] coupling of sulfur ylides with 2-nitrobenzofurans. This reaction proceeds smoothly under mild conditions, yielding the desired products in moderate to good yields without the need for precious catalysts or additives. The reutilization of the departed nitro-anion during the reaction process enables a high atom economy and leads to the formation of products with a complex structure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chengkou Liu, Yang Lin, Chen Cai, Chengcheng Yuan, Zheng Fang, Kai Guo
Summary: An unprecedented method has been developed for the straightforward electro-oxidative coupling of sulfides with activated methylene compounds to synthesize sulfur ylides, achieving good to excellent yields without the need for catalysts or oxidants at room temperature. This green and practical electrosynthesis, utilizing continuous-flow electrochemical setups, is highly efficient, exhibits excellent functional group tolerance, and can be easily scaled up.
Article
Chemistry, Multidisciplinary
Prithwish Ghosh, Na Yeon Kwon, Saegun Kim, Sangil Han, Suk Hun Lee, Won An, Neeraj Kumar Mishra, Soo Bong Han, In Su Kim
Summary: This method describes the unprecedented C(sp(2))-H methylation of iminoamido heterocycles as nucleoside base analogues, using trimethylsulfoxonium salt as a methylating agent under aqueous conditions. It achieves a wide substrate scope and excellent level of functional-group tolerance, and can be readily applied to site-selective methylation of azauracil nucleosides, highlighting its synthetic potential.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Tatyana S. Zhuk, Oleksandra S. Skorobohatko, Wendell Albuquerque, Holger Zorn
Summary: Basidiomycetous fungi were screened for their reductive activity towards carbonyl compounds, with some strains showing high activities towards aromatic carbonyls and aliphatic ketones. Utilizing whole-cell cultures of Dichomitus albidofuscus, the reactions were successfully scaled up to a preparative level with excellent selectivities and high yields of the respective alcohols. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions, with specific acids yielding benzyl alcohol, vanillin, dihydroconiferyl alcohol, and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bedrich Formanek, Vit Seferna, Marta Meazza, Ramon Rios, Mahendra Patil, Jan Vesely
Summary: This study reports the organocatalytic amination of pyrazol-5-ones with azodicarboxylates catalyzed by quinine, yielding enantiomerically enriched hydrazine adducts with quaternary stereocenters in high yields and enantioselectivities. Theoretical calculations help propose the relationship between the quinine catalyst and reactants, explaining the observed stereochemical outcome and trends in reaction effectiveness.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Georgia Poulladofonou, Kevin Neumann
Summary: Zwitterionic polymers have significant applications in biomedical science and nanotechnology. However, the existing designs are mostly limited to polybetaines and polyampholytes. This study introduces a new class of zwitterionic polymers, poly(sulfur ylides), which demonstrate remarkable stability and unique solution and thermal behavior.
Article
Chemistry, Organic
Roman O. Iakovenko, Daniel Chrenko, Jozef Kristek, Eline Desmedt, Frantisek Zalesak, Freija De Vleeschouwer, Jiri Pospisil
Summary: A new method for direct oxidative coupling of heteroaryl thiols and primary amines is reported. The readily available and inexpensive materials, mild reaction conditions, and good yields make it a useful tool for the synthesis of previously difficult to obtain sulfonamides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Wenjing Yu, Chen-Ho Tung, Zhenghu Xu
Summary: The synthesis of benzofurans from readily accessible sulfur ylides and ortho-hydroxy aryl alkynes is reported. The reaction proceeds through an isomerization/nucleophilic addition/cyclization/aromatization cascade, and the substrate scope is very broad with high yields obtained. The reaction conditions do not require the use of catalysts or additives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Sharada S. Labadie, Karine Thai, Jessica M. Grandner, Yanzhou Liu, Brendan T. Parr
Summary: This investigation demonstrates that enyne amides can smoothly undergo cyclization to form pyridones in the presence of a secondary amine, but fails with six-membered and larger ring systems. The ring closure reaction is catalytic, involving sequential 1,6-addition of the amine, 6-exo-trig ring closure of the iminium intermediate, and subsequent elimination of the secondary amine.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Lijie Zhang, Ling Fang, Hao Huang, Chaofan Wang, Fang Gao, Zhiyong Wang
Summary: The study presents a novel and reliable method for synthesizing biologically interesting benzo[e][1,4]thiazepine derivatives in synthetically useful yields. Postsynthetic modification also leads to the formation of its sulfoxide and sulfone derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Radell Echemendia, Matheus P. De Jesus, Lucas G. Furniel, David Philip Day, Antonio C. B. Burtoloso
Summary: Sulfoxonium ylides have been proven to play a versatile role in the synthesis of organic molecules. This study reports a new oxidative reaction mediated by molecular iodine to synthesize sterically encumbered arylated sulfoxonium ylides, resulting in the formation of 1,2-dicarbonyl containing compounds. The reaction displayed high efficiency, short reaction time, mild reaction conditions, and environmental friendliness.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dada S. Timofeeva, Armin R. Ofial, Herbert Mayr
Article
Chemistry, Multidisciplinary
Allison M. Dennis, Matthew R. Buck, Feng Wang, Nicolai F. Hartmann, Somak Majumder, Joanna L. Casson, John D. Watt, Stephen K. Doorn, Han Htoon, Milan Sykora, Jennifer A. Hollingsworth
ADVANCED FUNCTIONAL MATERIALS
(2019)
Article
Chemistry, Organic
Robert J. Mayer, Martin Breugst, Nathalie Hampel, Armin R. Ofial, Herbert Mayr
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Multidisciplinary Sciences
Nicolai F. Hartmann, Matthew Otten, Igor Fedin, Dmitri Talapin, Moritz Cygorek, Pawel Hawrylak, Marek Korkusinski, Stephen Gray, Achim Hartschuh, Xuedan Ma
NATURE COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Hyejin Kwon, Mijin Kim, Manuel Nutz, Nicolai F. Hartmann, Vivien Perrin, Brendan Meany, Matthias S. Hofmann, Charles W. Clark, Han Htoon, Stephen K. Doorn, Alexander Hoegele, YuHuang Wang
ACS CENTRAL SCIENCE
(2019)
Article
Chemistry, Multidisciplinary
Mohanad A. Hussein, Uyen P. N. Tran, Vien T. Huynh, Junming Ho, Mohan Bhadbhade, Herbert Mayr, Thanh V. Nguyen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Feng An, Biplab Maji, Elizabeth Min, Armin R. Ofial, Herbert Mayr
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Robert J. Mayer, Armin R. Ofial, Herbert Mayr, Claude Y. Legault
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Jingjing Zhang, Quan Chen, Robert J. Mayer, Jin-Dong Yang, Armin R. Ofial, Jin-Pei Cheng, Herbert Mayr
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Zhen Li, Robert J. Mayer, Armin R. Ofial, Herbert Mayr
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Biographical-Item
Chemistry, Multidisciplinary
Bernd Giese, Herbert Mayr, Hans-Ulrich Reissig
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Lukas Grossmann, Benjamin T. King, Stefan Reichlmaier, Nicolai Hartmann, Johanna Rosen, Wolfgang M. Heckl, Jonas Bjork, Markus Lackinger
Summary: The study focuses on the synthesis of ordered porous two-dimensional polymers on alkane-passivated graphite surfaces through two-staged photopolymerization. The highly ordered monolayer structures are first formed by self-assembly, followed by complete covalent cross-linking induced by violet light irradiation.
Article
Chemistry, Organic
Manfred Hartnagel, Armin R. Ofial, Herbert Mayr
SYNTHESIS-STUTTGART
(2023)
Article
Materials Science, Multidisciplinary
Ali Semerci, Ali Buyruk, Saim Emin, Rik Hooijer, Daniela Kovacheva, Peter Mayer, Manuel A. Reus, Dominic Blaette, Marcella Guenther, Nicolai F. Hartmann, Soroush Lotfi, Jan P. Hofmann, Peter Mueller-Buschbaum, Thomas Bein, Tayebeh Ameri
Summary: Recently, interest in mixed-dimensional (3D/2D or 3D/1D) perovskite solar cells using small organic spacers has grown due to their excellent long-term stability. This study presents a new type of thiophene-based organic cation, ThPyI, which is utilized for fabricating mixed-dimensional 3D/1D perovskite solar cells. The ThPyI-based 1D perovskitoid acts as a passivant at the grain boundaries, improving the power conversion efficiency (PCE) of the solar cells. These findings provide new insights into the design of organic spacers and passivation strategies for defect mitigation in hybrid 3D/1D perovskite solar cells.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Multidisciplinary Sciences
Rui Zeng, Lei Zhu, Ming Zhang, Wenkai Zhong, Guanqing Zhou, Jiaxing Zhuang, Tianyu Hao, Zichun Zhou, Libo Zhou, Nicolai Hartmann, Xiaonan Xue, Hao Jing, Fei Han, Yiming Bai, Hongbo Wu, Zheng Tang, Yecheng Zou, Haiming Zhu, Chun-Chao Chen, Yongming Zhang, Feng Liu
Summary: This study demonstrates a thin film organic photovoltaic technology integrated with nano-sized phase separation and micro-sized surface topology, which can harvest solar energy at different incident angles throughout the day. The all-polymer solar cells with hierarchical morphology and large light-receiving angle are suitable for commercial applications of distributed photovoltaics.
NATURE COMMUNICATIONS
(2023)