Article
Chemistry, Organic
Irene Paramio, Tomas Torres, Gema de la Torre
Summary: In this work, a smart approach to enhance the reactivity towards self-condensation of binaphthol-bridged phthalonitriles was reported, which relies on the addition of another highly reactive phthalonitrile. By optimizing the reaction conditions, a high-yield ethynyl-containing binaphthyloxy-bridged Zn(ii)Pc was obtained, which has the ability to form nanostructures in aqueous solutions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
John Hartung, Xiang Wang, Zhiguo Jake Song, You Chen, Feng Guo, Zhifeng Li
Summary: Palladium-catalyzed cyanation is an important method for installing functional groups commonly found in active pharmaceutical ingredients. In this study, a robust cyanation reaction was developed with full conversion achieved at a catalyst loading as low as 0.13 mol%, which was affected by trace water levels. The scale-up of this process to a hundred-kilogram batch size is also described.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Applied
Dmitry A. Bunin, Alexander G. Martynov, Evgeniya A. Safonova, Aslan Yu. Tsivadze, Yulia G. Gorbunova
Summary: A new synthetic pathway has been developed for water-soluble phthalocyanines with cationic groups. These compounds exhibit strong absorption in the phototherapeutical spectral range and high quantum yields of singlet oxygen generation. Some complexes exist in monomeric forms in water.
Article
Chemistry, Multidisciplinary
Yanan Hou, Hui Wang, Juan Xi, Ruonan Jiang, Lizhi Zhang, Xinjin Li, Fenggang Sun, Qing Liu, Zengdian Zhao, Hui Liu
Summary: Since the development of palladium-catalyzed cyanation in 1973, there has been widespread interest in the transition metal-catalyzed cyanation of aryl halides using Pd, Ni, and Cu. However, these reactions require highly polar organic solvents and high temperatures. In this study, we have developed a non-toxic K-4[Fe(CN)(6)]-promoted mechanochemical palladium-catalyzed solid-state cyanation of aryl bromides using an electromagnetic mill (EMM) without additional heating. This strategy offers a broad substrate scope, good functional group tolerance, liquid-assisted grinding, air and moisture insensitivity, no additional heating requirement, and efficient gram-scale synthesis.
Article
Chemistry, Organic
Hua Yao, Xiaoyang Zhong, Bingqing Wang, Sen Lin, Zhaohua Yan
Summary: A novel and efficient approach for the amine-directed dehydrogenative C(sp(2))-C(sp(3)) coupling of arylamines with acetonitrile was developed using FeCl2 as the catalyst. The method provides a straightforward and green route to arylacetonitriles with good regioselectivity and excellent compatibility of functional groups and aromatic rings.
Article
Chemistry, Organic
Chongjiu Lu, Min Ye, Lipeng Long, Yue Zheng, Jiameng Liu, Yue Zhang, Zhengwang Chen
Summary: An efficient formal alkenyl C-H cyanation reaction has been developed for the synthesis of unsymmetrical diarylfumaronitriles. The advantages of this transformation include the use of a safe and non-toxic cyanide source, absence of external noble metal catalyst, easy availability of raw materials, good functional group tolerance, high stereoselectivity, and potential further application of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xianqiang Kong, Yuchang Wang, Yiyi Chen, Xiaohui Chen, Long Lin, Zhong-Yan Cao
Summary: A practical and mild electrochemical protocol has been developed for cyanation and cyanomethylation of trimethylammonium salts through C-N bond cleavage without the need for external stoichiometric reducing agents or sacrificial anodes. The reaction shows high functional group compatibility and can be used for the synthesis of natural product derivatives. Preliminary mechanistic studies suggest the involvement of a radical addition pathway.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Farzaneh Karimi, Masoumeh Jadidi Nejad, Arefe Salamatmanesh, Akbar Heydari
Summary: A highly efficient heterogeneous copper catalyst was developed by supporting copper acetate on a magnetically separable triazine-vitamin B-5 system. The prepared nanoparticles were characterized by various techniques and showed favorable catalytic efficiency in the cyanation reaction of aryl halides using nitromethane as a non-toxic and cost-effective cyanation source. The magnetic nanocatalyst could be easily recovered and reused multiple times without significant performance decrease.
Article
Chemistry, Organic
Bhargava Rao Billa, Chih-Hsiu Lin
Summary: The study successfully synthesized six stable and soluble electron acceptors using specific synthetic methods, with LUMO energy levels comparable to benchmark compounds. Additionally, the research found that each additional nitrile group reduces the LUMO energy by 0.2 eV.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Mohammad Gholinejad, Mohammad Shojafar, Jose M. Sansano, Vladimir N. Mikhaylov, Irina A. Balova, Rahimeh Khezri
Summary: This article presents a new nitrogen-rich hyperbranched polymer PolyTZ-IL@Pd NPs used for stabilizing Pd nanoparticles, showing efficient catalytic performance in the reduction of nitroarenes and cyanation of aryl bromides and iodides.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kai Wang, Jiahua Wang, Wenkai Yuan, Xiang-Ying Tang, Long Wang
Summary: Divergent synthetic methods were developed for transforming isatins to 2-cyanoaryl carbamate and 2-cyanoaryl urea derivatives, using ammonium carbamate as the nitrogen source and iodobenzene diacetate as the oxidant. This method features mild conditions, broad substrate scope, and the avoidance of toxic cyano-containing compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kai Wang, Jiahua Wang, Wenkai Yuan, Xiang-Ying Tang, Long Wang
Summary: Divergent synthetic methods for converting isatins to 2-cyanoaryl carbamate and 2-cyanoaryl urea derivatives were developed, utilizing ammonium carbamate as the nitrogen source and iodobenzene diacetate as the oxidant. This reaction offers mild conditions, a wide range of substrate adaptability, and avoids the use of toxic cyano-containing compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Debra J. Wallace, Thomas Storz, Anna Balanov, William S. Kissel
Summary: This paper presents an efficient, robust, and scalable synthesis of CY6463, the first CNS-penetrant sGC stimulator, allowing for rapid generation of larger quantities of material to accelerate early clinical studies while minimizing resource use. The synthesis involves a palladium-catalyzed one-pot reaction and a novel triazole formation method.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Ting Cui, Yanling Zhan, Changhui Dai, Jun Lin, Ping Liu, Peipei Sun
Summary: An electrochemical oxidative regioselective C-H cyanation of imidazo[1,2-a]pyridines was developed utilizing TMSCN as the cyano source, with the KH2PO4/K2HPO4 buffer being essential for the transformation. This protocol was compatible with a broad range of substituted imidazo[1,2-a]pyridines and provided the C3 cyanated products in moderate to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
G. Sudhakar Reddy, E. J. Corey
Summary: This article presents short synthetic routes to the nonplanar tetracyclic ketiminium salt A and two similar compounds. X-ray crystallography confirms their helical nonplanar structures.
Article
Chemistry, Medicinal
Shi Qiu, Kourosch Abbaspour Tehrani, Sergey Sergeyev, Patrick Bultinck, Wouter Herrebout, Benoit Mathieu
Article
Chemistry, Organic
Yan-Ping Zhu, Sergey Sergeyev, Philippe Franck, Romano V. A. Orru, Bert U. W. Maes
Article
Chemistry, Applied
Dominic Ormerod, Nicolas Lefevre, Matthieu Dorbec, Inge Eyskens, Pieter Vloemans, Karlien Duyssens, Veronica Diez de la Torre, Nadya Kaval, Eugen Merkul, Sergey Sergeyev, Bert U. W. Maes
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2016)
Article
Chemistry, Multidisciplinary
Jorge S. Valera, Rafael Gomez, Luis Sanchez
Article
Chemistry, Physical
Pieter Mampuys, Helfried Neumann, Sergey Sergeyev, Romano V. A. Orru, Haijun Jiao, Anke Spannenberg, Bert U. W. Maes, Matthias Beller
Article
Chemistry, Multidisciplinary
Valery A. Ozeryanskii, Marina P. Vlasenko, Alexander F. Pozharskii, Sergey Sergeyev, Bert U. W. Maes, Philippe Franck, Wouter A. Herrebout
Article
Chemistry, Applied
Dominic Ormerod, Matthieu Dorbec, Eugen Merkul, Nadya Kaval, Nicolas Lefevre, Steven Hostyn, Lies Eykens, Jo Lievens, Sergey Sergeyev, Bert U. W. Maes
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2018)
Article
Chemistry, Multidisciplinary
Zoltan Dobi, B. Narendraprasad Reddy, Evelien Renders, Laurent Van Raemdonck, Carl Mensch, Gilles De Smet, Chen Chen, Charles Bheeter, Sergey Sergeyev, Wouter A. Herrebout, Bert U. W. Maes
Article
Chemistry, Multidisciplinary
Enguerrand Blondiaux, Jeroen Bomon, Michal Smolen, Nadya Kaval, Filip Lemiere, Sergey Sergeyev, Ludo Diels, Bert Sels, Bert U. W. Maes
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2019)
Article
Chemistry, Multidisciplinary
Jeroen Bomon, Elias Van Den Broeck, Mathias Bal, Yuhe Liao, Sergey Sergeyev, Veronique Van Speybroeck, Bert F. Sels, Bert U. W. Maes
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Gilles De Smet, Xingfeng Bai, Carl Mensch, Sergey Sergeyev, Gwilherm Evano, Bert U. W. Maes
Summary: This study demonstrates that acetate can serve as a renewable leaving group for selective deoxygenation of phenolics. The Ni-catalyzed reaction in a green solvent allows for efficient deoxygenation without affecting specific functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jeroen Bomon, Mathias Bal, Tapas Kumar Achar, Sergey Sergeyev, Xian Wu, Ben Wambacq, Filip Lemiere, Bert F. Sels, Bert U. W. Maes
Summary: The demethylation reaction of aromatic methyl ethers using mineral acid as a catalyst in high temperature pressurized water provides high yields of aromatic alcohols. Versatility of the method was demonstrated on various substrates, with up to 99% yield of aromatic alcohols in most cases. The method is scalable and can utilize biorenewable feedstock like wood and clove oil.
Article
Chemistry, Multidisciplinary
Jorge S. Valera, Roberto Sanchez-Naya, Francisco J. Ramirez, Jose L. Zafra, Rafael Gomez, Juan Casado, Luis Sanchez
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Applied
Yan-Ping Zhu, Pieter Mampuys, Sergey Sergeyev, Steven Ballet, Bert U. W. Maes
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Benedicte Morel, Philippe Franck, Johan Bidange, Sergey Sergeyev, Dan A. Smith, Jonathan D. Moseley, Bert U. W. Maes
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.
