Article
Chemistry, Multidisciplinary
En Li, Kai Tang, Zhuhui Ren, Xiaoyun Liao, Qianchen Liu, Yong Huang, Jiean Chen
Summary: The successful enantioselective beta-alkylation of homoenolates using C-sp3 electrophiles through an S(N)2 strategy is reported. The method shows a broad scope and delivers good yields and excellent enantioselectivities (up to 99% ee). It enables the installation of drug-like structural motifs and presents a concise synthetic route to chiral pyrroloindoline-type skeletons. Preliminary mechanistic studies support a direct S(N)2 mechanism.
Article
Chemistry, Physical
Zhen Li, Meirong Huang, Xinhao Zhang, Jiean Chen, Yong Huang
Summary: This study reports an organocatalytic four-component relay radical coupling to access a broad spectrum of beta-tertiary-gamma-quaternary carboxylic acid derivatives, overcoming the synthetic bottleneck of introducing sterically demanding side chains. The high site control achieved using a triazolium N-heterocyclic carbene catalyst and a transient acyl trapping strategy allows for the preparation of diversified carboxylic acid derivatives in a single pot.
Article
Chemistry, Inorganic & Nuclear
Ximena Zarate, Lucian-Cristian Pop, Manuel Treto-Suarez, Jorge Tapia, Eduardo Schott
Summary: This study investigated the aromatic properties of gold benzimidazole and cycloheptaimidazole N-heterocyclic carbenes through computational calculations, revealing a minor difference between the two families with family 1 being slightly more aromatic. The high stability of the gold atom's molecular orbitals in the complexes resulted in almost no contribution from the metal to the observed UV-Vis transitions.
Article
Chemistry, Multidisciplinary
Arne Merschel, Dennis Rottschaefer, Beate Neumann, Hans-Georg Stammler, Mark Ringenberg, Maurice Van Gastel, T. Ilgin Demirer, Diego M. M. Andrada, Rajendra S. S. Ghadwal
Summary: In this study, we have successfully synthesized and isolated two stable anions K[SIPrBp] (4 a-K) and K[IPrBp] (4 b-K). These anions, derived from classical N-heterocyclic carbenes (NHCs), exist as violet crystalline solids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ryuji Kyan, Yuya Kitagawa, Ryuji Ide, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
Summary: The study demonstrates the use of highly sterically hindered N-heterocyclic carbenes as catalysts in the cross-annulation reaction of alpha,beta-enals and aryl aldehydes, leading to the convergent construction of beta,gamma-trans-disubstituted gamma-butyrolactones.
Article
Chemistry, Multidisciplinary
Hang Shen, Michael B. Larsen, Allison G. Roessler, Paul M. Zimmerman, Andrew J. Boydston
Summary: A new flex-activated mechanophore has been discovered, which releases an N-heterocyclic carbene (NHC) under mechanical load. This design demonstrates a promising first step towards flex-activated designs with downstream reactivities, allowing for iterative activation increases in the material through non-destructive compression cycles. The potential modularity of the mechanophore design is highlighted by the demonstration of two different NHC structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Zhen Li, Pengju Ji, Jin-Pei Cheng
Summary: A Brønsted basicity scale was established for nine representative N-heterocyclic olefins (NHOs) using an UV-visible spectroscopic method. The unsaturated NHOs were found to have stronger basicities compared to their N-heterocyclic carbene (NHC) analogues, while the basicities of the saturated NHOs were weaker. The nucleophilicity of the NHOs was also stronger than commonly used Lewis bases but weaker than their NHC analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ludwig Zapf, Udo Radius, Maik Finze
Summary: The paper describes the synthesis of 1,3-bis(tricyanoborane)imidazolate anion and its derivatives, including a novel dianionic N-heterocyclic carbene. These compounds exhibit unique electronic and steric properties, making them promising ligands and building blocks for coordination chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Junbeom Park, Jaelim Kim, Gu Yoon Jeong, Youngsuk Kim, Eunsung Lee
Summary: This study investigates the electron and proton transfer chemistry of N-heterocyclic carbene nitric oxide radical compounds and prepares a variety of nitrosyl derivatives. The reactions of these derivatives resemble those of transition metal nitrosyl complexes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Oncology
Prasad Dandawate, Khursheed Ahmed, Subhash Padhye, Aamir Ahmad, Bernhard Biersack
Summary: Recent research has shown that simply prepared chalcones have promising anti-tumor activities, including a considerable number of tubulin polymerization inhibitors and new chalcones targeting specific enzymes or with DNA-binding properties. This review provides a summary of recent heterocyclic chalcone derivatives with distinct anti-tumor activities.
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(2021)
Article
Biochemical Research Methods
Fady Nahra, Nikolaos Tzouras, Alba Collado, Steven P. Nolan
Summary: N-heterocyclic carbene gold(I) chloride and hydroxide complexes are commonly used as synthetic reagents and efficient catalysts. This study describes a straightforward and practical method for synthesizing mononuclear gold complexes with high yields, as well as the synthesis of a mononuclear gold(I) hydroxide complex and an improved synthesis method for a dinuclear gold(I) hydroxide complex. This methodology offers advantages such as the use of sustainable reaction solvents and commercially available starting materials.
Review
Chemistry, Multidisciplinary
Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.
SCIENCE CHINA-CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kun-Quan Chen, He Sheng, Qiang Liu, Pan-Lin Shao, Xiang-Yu Chen
Summary: In recent years, NHC-catalyzed radical reactions have been gaining attention for their potential to create new activation modes previously inaccessible. Further research and understanding of this emerging area is warranted to explore its synthetic techniques and advantages.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nadine Weyer, Myron Heinz, Julia I. Schweizer, Clemens Bruhn, Max C. Holthausen, Ulrich Siemeling
Summary: The N-heterocyclic silylene shows a remarkable combination of thermal stability and reactivity towards small molecules, producing different follow-up products in reactions with CO2, N2O, H2O, NH3, and FcPH(2). Unexpectedly, the reaction with H3BNH3 results in B-H activation instead of N-H activation. DFT results suggest dramatically different mechanisms for these H-X insertions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Theo Maulbetsch, Doris Kunz
Summary: The synthesis of a novel NHC-containing porphyrinoid ligand with good fluorescence properties was successfully achieved. Experimental results demonstrated that the heterocyclic moieties in both the ligand and its metal complexes exhibit aromatic character instead of antiaromatic macrocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
N. Aiswarya, M. Sithambaresan, S. S. Sreejith, Seik Weng Ng, M. R. Prathapachandra Kurup
INORGANICA CHIMICA ACTA
(2016)
Article
Chemistry, Inorganic & Nuclear
S. S. Sreejith, Nithya Mohan, N. Aiswarya, M. R. Prathapachandra Kurup
Article
Chemistry, Inorganic & Nuclear
Roji J. Kunnath, M. Sithambaresan, A. Ambili Aravindakshan, Aiswarya Natarajan, M. R. Prathapachandra Kurup
Article
Chemistry, Organic
Jagadeesh Krishnan, C. R. Sinu, M. Anusree, K. C. Seetha Lakshmi, T. S. Mayadevi, Suresh Eringathodi, Vijay Nair
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Acoustics
Joachim Demaerel, Sebastian Govaerts, Rony Rajan Paul, Tom Van Gerven, Wim M. De Borggraeve
ULTRASONICS SONOCHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Joseph P. Campbell, Sinu C. Rajappan, Tyler J. Jaynes, Mona Sharafi, Yong-Tao Ma, Jianing Li, Severin T. Schneebeli
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Sinu C. Rajappan, Dillon R. McCarthy, Joseph P. Campbell, Jonathon B. Ferrell, Mona Sharafi, Ona Ambrozaite, Jianing Li, Severin T. Schneebeli
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Mona Sharafi, Kyle T. McKay, Monika Ivancic, Dillon R. McCarthy, Natavan Dudkina, Kyle E. Murphy, Sinu C. Rajappan, Joseph P. Campbell, Yuxiang Shen, Appala Raju Badireddy, Jianing Li, Severin T. Schneebeli
Article
Polymer Science
Sinu C. Rajappan, Brad J. Davis, Travis L. Thornell, Yoan C. Simon
Summary: The study presents the synthesis of a new aliphatic azo-containing polyurethane and its degradation behavior under different external stimuli, highlighting the importance of radical activity in azo-containing polymers. The results reveal the dependencies of monomer and radical stability in the controlled degradation process.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Polymer Science
Sinu C. Rajappan, Brad J. Davis, Isaiah T. Dishner, Travis L. Thornell, John J. Peyrefitte, Yoan C. Simon
Summary: We have developed a new amine-hardener that enables thermal activated healing in epoxy-amine coatings. A hetero-Diels Alder (HDA) adduct acts as a thermoreversible linker, bridging biosourced fatty acids. Validating the thermal reversion of the adduct in solution, the HDA-containing diamine is a drop-in replacement for commercial hardeners.
Review
Chemistry, Multidisciplinary
Roop Varghese Rubert, Rony Rajan Paul
Summary: The design and implementation of flow technique have proven to be valuable tools for organic chemists to tackle challenges encountered during catalytic reactions. Over the last two decades, flow technologies have gained popularity in the field of organic chemistry as they provide solutions for technical and/or chemical issues. Flow reactors improve the selectivity, efficiency, and safety of the entire process by enhancing mass and heat transfer, promoting mixing of reactions, and offering precise control of reaction parameters. This review focuses on the utilization of flow chemistry in reactions involving organozinc reagent, particularly Negishi coupling, which is widely used in total synthesis for the formation of C-C bonds with functional group tolerance. The review also includes a comparative study of organozinc reagents prepared using different procedures and investigates the effect of different catalysts on the same reaction. Additionally, it provides an overview of various flow techniques employed in this area.
JOURNAL OF FLOW CHEMISTRY
(2023)
Correction
Chemistry, Multidisciplinary
Roop Varghese Rubert, Rony Rajan Paul
JOURNAL OF FLOW CHEMISTRY
(2023)
Review
Chemistry, Physical
David Aili, Mikkel Rykaer Kraglund, Sinu C. Rajappan, Dmytro Serhiichuk, Yifan Xia, Valadoula Deimede, Joannis Kallitsis, Chulsung Bae, Patric Jannasch, Dirk Henkensmeier, Jens Oluf Jensen
Summary: Water electrolysis for hydrogen production is crucial in achieving the green transition and developing sustainable fuels and materials. Alkaline water electrolysis is a key technology in this field as it is not limited by the scarcity of resources. However, the renewable energy system demands higher energy efficiency, rate capability, and operational capability. New electrode separators that can support high currents and suppress gas crossover are essential for these advancements.
ACS ENERGY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Mona Sharafi, Joseph P. Campbell, Sinu C. Rajappan, Natavan Dudkina, Danielle L. Gray, Toby J. Woods, Jianing Li, Severin T. Schneebeli
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Crystallography
S. Sravya, S. Sruthy, N. Aiswarya, M. Sithambaresan, M. R. Prathapachandra Kurup
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
