Article
Chemistry, Organic
Daisuke Mishima, Haruka Nakanishi, Yui Tsuboi, Yusho Kishimoto, Yohei Yamanaka, Ai Harada, Masahiro Togo, Yuto Yamada, Masahiro Muraoka, Michihisa Murata
Summary: This study reports a domino-type multiple C-H functionalization of tetracene with molecular benzene, forming eight C-C bonds through oxidative cross-dehydrogenative coupling without the mediation of a metal catalyst or a specific substituent.
Article
Chemistry, Organic
Ryo Kurose, Yuji Nishii, Masahiro Miura
Summary: An efficient synthetic method for the electrophilic trifluoromethylthiolation of aromatic compounds is reported, utilizing triptycenyl sulfide (Trip-SMe) and TfOH to enhance the electrophilicity of SCF3 fragment through the formation of sulfonium intermediates. This method enables direct installation of an SCF3 group onto unactivated aromatics at room temperature, using a commercially available saccharin-based reagent. Preliminary DFT calculation was conducted to investigate the substitution effect on the catalytic activity.
Article
Chemistry, Organic
Pragati Biswal, Tanmayee Nanda, Namrata Prusty, Smruti Ranjan Mohanty, Ponneri C. Ravikumar
Summary: A rhodium-catalyzed oxidative C-H/N-H dehydrogenative[3 + 2] annulation strategy has been developed for the synthesis of 2-methylindole scaffolds by reacting anilines and N-allylbenzimidazole. This transformation involves the cleavage of the thermodynamically stable C-N bond of allylamine and proceeds through a cascade of C(sp(2))-H alkylation followed by intramolecular cyclization. Detailed mechanistic studies have been performed to identify a key intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ke Fang, Wenyi Huang, Chunxiao Shan, Jingping Qu, Yifeng Chen
Summary: A novel nickel-catalyzed reaction method for the synthesis of 3,3-dialkyl-substituted isoindolinone frameworks from unactivated alkyl iodides and 1,1-disubstituted enamides has been reported. The method exhibits good functional group tolerance and enantioselectivity through the use of commercially available chiral Bn-Biox ligand.
Article
Chemistry, Multidisciplinary
Rene S. Bitsch, Nicolaj Inunnguaq Jessen, Karl Anker Jorgensen
Summary: Cycloadditions are important reactions in materials science for constructing polycyclic aromatic and heteroaromatic compounds. Recent developments in organocatalysis have allowed for the control of cycloadditions involving an extended number of pi-electrons. This field, known as higher-order cycloadditions, enables the synthesis of polycyclic carbo- and heteroaromatic compounds in two or three dimensions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Ashley Dang-Nguyen, Kristine C. Legaspi, Connor T. McCarty, Diane K. Smith, Jeffrey Gustafson
Summary: We present a practical, light-mediated perfluoroalkylation method using Langlois' reagent that does not require any photocatalyst or additives. This method allows for easy functionalization of pyridones and related N-heteroarenes such as azaindole. The protocol is straightforward, utilizes readily available materials, and is compatible with both electron-neutral and -rich pyridones.
Article
Chemistry, Organic
Jie Li, Xinhui Zhang, Yisen Yao, Yapei Gao, Wen Yang, Wanxiang Zhao
Summary: An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction has been developed for the synthesis of oxygen atom-substituted allylboronates with aryl/vinyl bromides, iodides, and triflates. This protocol offers a broad substrate scope, excellent functional group tolerance, and easy gram-scale preparation, providing an alternative approach for the synthesis of allylic alcohols and their derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Environmental Sciences
Cameron P. Oden, Charles J. Werth, Benjamin A. Kienzle, Lynn E. Katz
Summary: Thermal remediation is an effective technology for removing contaminants from soil, but it is costly and inefficient. This study investigates the role of organic matter in the removal process and identifies possible reaction mechanisms. The results show that contaminant transformation contributes significantly to removal even at lower temperatures.
SCIENCE OF THE TOTAL ENVIRONMENT
(2024)
Article
Chemistry, Organic
Jayanta Dey, Subhasis Paul, Manotosh Bhakat, Joyram Guin
Summary: In this study, a photocatalytic method was developed for the direct incorporation of an oxime functional group at inert C(sp3)-H bonds of ethers, amides, alcohols, amines, and alkanes. The method utilizes air and a blue LED to enable hydrogen atom transfer with photoexcited eosin Y under mild conditions. The reaction tolerates many useful functional groups and is scalable. Mechanistic studies were conducted to support the proposed radical pathway for the process.
Article
Spectroscopy
Lucia M. Lepodise, Romang Bosigo
Summary: The study of soil samples from Botswana revealed the presence of aromatic compounds, with higher pH values and mainly consisting of magnesium and calcium as major nutrients.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2022)
Article
Chemistry, Multidisciplinary
Koki Horii, Ryohei Kishi, Masayoshi Nakano, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Akihito Konishi, Makoto Yasuda
Summary: Bis-periazulene and its derivatives exhibit unique electronic structures and energy states, providing potential applications in extended π-conjugated systems.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Xuefeng Lu, Dongyue An, Yi Han, Ya Zou, Yanjun Qiao, Ning Zhang, Dongdong Chang, Jishan Wu, Yunqi Liu
Summary: A novel cyclopenta-fused macrocyclic tetraradicaloid, MC4-S, containing alternating phenanthrene and dibenzo[b,d]thiophene units, was synthesized and characterized. The two sulfur atoms in MC4-S lead to a smaller radical character and a larger singlet-triplet energy gap compared to its all-carbon isoelectronic structure, CPTP-M. X-ray crystallographic analysis revealed stronger spin-spin coupling through the DBTh unit than through the Phen moiety. The presence of electron-rich sulfur atoms raised the energies of both the HOMO and LUMO in MC4-S, while overall optical and electronic energy gaps remained similar to CPTP-M.
Article
Chemistry, Organic
Xiang Li, Danlu Li, Xiaofei Zhang
Summary: A Ru(ii)-catalyzed C-H bond activation/annulation reaction of N-iminopyridinium ylides with sulfoxonium ylides has been developed for the synthesis of diverse functionalized isocoumarin derivatives. This method shows broad substrate scope, excellent functional group tolerance, simple operation, and silver salt-free conditions. Furthermore, the utility of this method is demonstrated by the alkenylation of the product and efficient synthesis of biologically active thunberginol A.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biology
Chrats Melkonian, Lucas Fillinger, Siavash Atashgahi, Ulisses Nunes da Rocha, Esther Kuiper, Brett Olivier, Martin Braster, Willi Gottstein, Rick Helmus, John R. Parsons, Hauke Smidt, Marcelle van der Waals, Jan Gerritse, Bernd W. Brandt, Wilfred F. M. Roeling, Douwe Molenaar, Rob J. M. van Spanning
Summary: Researchers used metagenomics and transcriptomics to study microbial dynamics in a 15-year old bioreactor with benzene as the main carbon source. Their findings revealed that most members of the microbial community likely feed on metabolic leftovers or necromass, while only a few are capable of degrading benzene. These benzene degraders are essential for maintaining species richness and ecosystem stability within the community.
COMMUNICATIONS BIOLOGY
(2021)
Review
Environmental Sciences
Jamie M. Dearnley, Charles Killeen, Rebecca L. Davis, Vince P. Palace, Gregg T. Tomy
Summary: This article reviews the metabolism and toxicity of polycyclic aromatic compounds (PACs) in fish and presents various methods for analyzing metabolite-containing bile. Recent environmental monitoring studies demonstrate the utility of this technique in assessing oil spill pollution, establishing baseline exposure, and evaluating pollution in urban waterways.
CRITICAL REVIEWS IN ENVIRONMENTAL SCIENCE AND TECHNOLOGY
(2022)
Article
Chemistry, Organic
Andrey Puzanov, Dmitry S. Ryabukhin, Anna S. Zalivatskaya, Dmitriy N. Zakusilo, Darya S. Mikson, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: Novel acetylene derivatives of 1,2,4-oxadiazoles were successfully synthesized and their reactivity towards arenes in triflic acid was studied.
Formation of E/Z-vinyl triflates from the acetylene bond of oxadiazoles was achieved, providing insights into the reaction mechanisms.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yelizaveta Gorbunova, Dmitry S. Ryabukhin, Aleksander V. Vasilyev
Summary: The reaction between 3-arylpropynenitriles and electron-rich arenes in the presence of aluminum bromide leads to the stereoselective formation of 3,3-diarylpropenenitriles, followed by cyclization into 3-arylindenones with high yields under triflic acid catalysis at room temperature.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anastasiya V. Igushkina, Alexander A. Golovanov, Aleksander V. Vasilyev
Summary: The reaction between linear conjugated enynones and 3-oxo-3-phenylpropanenitrile yields polyfunctional delta-diketones as regioselective Michael addition products. The obtained delta-diketones can further undergo heterocyclization with hydrazine, demonstrating their synthetic potential.
Article
Chemistry, Organic
Marina A. Borisova, Dmitry S. Ryabukhin, Alexander Yu Ivanov, Irina A. Boyarskaya, Dmitrii A. Shabalin, Lev E. Zelenkov, Elena Yu Schmidt, Boris A. Trofimov, Aleksander V. Vasilyev
Summary: 5-Hydroxy-1-pyrrolines react with arenes in TfOH or H2SO4 to afford 5-aryl-1-pyrrolines, and undergo dehydration in TfOH or H2SO4 to form N-protonated forms of 3H-pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Mikhail Kalyaev, Dmitry S. Ryabukhin, Marina A. Borisova, Alexander Yu Ivanov, Irina A. Boyarskaya, Kristina E. Borovkova, Lia R. Nikiforova, Julia Salmova, Nikolay Ul'yanovskii, Dmitry S. Kosyakov, Aleksander V. Vasilyev
Summary: The reactions of furan acids and esters with arenes in the presence of the superacid TfOH result in the formation of hydroarylation products. These compounds demonstrate antimicrobial activity against fungi Candida albicans, as well as inhibitory effects on Escherichia coli and Staphylococcus aureus.
Article
Chemistry, Organic
Olesya V. Khoroshilova, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: This study investigates the reaction of TMS ethers of CF3-benzyl alcohols and their heterocyclic analogues under the catalysis of strong acids, leading to the synthesis of alpha-(trifluoromethyl)styrenes and cis-/trans- 1,3-di(trifluoromethyl)indanes with high yields. The plausible reaction mechanisms, including the formation of CF3-benzyl carbocations as intermediates, are discussed.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Irina I. Ignatova, Olesya V. Khoroshilova, Aleksander V. Vasilyev
Summary: Reaction of 3-arylpropynoic acid derivatives and conjugated acetylene ketones with arenes and cyclohexane in the presence of AlCl3 at room temperature for 15 h results in one-pot tandem hydroarylation-ionic hydrogenation of the acetylene bond with yields ranging from 42% to 98%. This reaction is accompanied by aryl group exchange under acidic conditions.
MENDELEEV COMMUNICATIONS
(2023)
Article
Materials Science, Paper & Wood
Dmitriy N. Zakusilo, Edward I. Evstigneyev, Alexandr Yu Ivanov, Anton S. Mazur, Elena A. Bessonova, Oussama Abdelhamid Mammeri, Aleksander V. Vasilyev
Summary: The objective of this study was to determine the structures of oxidation products of hydrolysis lignin (HL) obtained in the H2O2-H2SO4-H2O system. The results revealed that the oxidized hydrolysis lignin (OHL) contained fragments of muconic acid dilactone. These fragments were formed through the oxidation of the aromatic ring of HL into unstable structures of 3,4-dihydroxyadipic acid, which cyclized into muconic acid dilactone in an acidic oxidative medium. Reaction of OHL with sodium hydroxide (NaOH) resulted in the formation of sodium salt of OHL (Na-OHL), in which the muconic acid dilactone units of OHL opened into disodium salts of 3,4-dihydroxyadipic acid. Na-OHL was further transformed into novel derivatives of lignins through reactions with thionyl chloride, amines, and alcohols.
JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY
(2023)
Article
Chemistry, Organic
Vladislav A. Sokolov, Andrei A. Golushko, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: This study discovers a method to transform trichloromethyl-substituted enones into trichloromethylindanones under superacidic conditions. It also discovers a method to convert trichloromethyl-hydroxy ketones into trichloromethylindanones under the same conditions.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Edward I. Evstigneyev, Dmitriy N. Zakusilo, Dmitry S. Ryabukhin, Aleksander V. Vasilyev
Summary: This review discusses the latest advances in lignin chemistry, including the structure, biosynthesis, and various methods for valorization of lignin.
RUSSIAN CHEMICAL REVIEWS
(2023)
Article
Chemistry, Organic
Oussama Abdelhamid Mammeri, Ilia M. Baranov, Alexandr Yu Ivanov, Irina A. Boyarskaya, Aleksander. V. Vasilyev
Summary: In this study, it was found that alkyl allene carboxylates can be efficiently cyclized to form 2-(5H)-furanones in the presence of Bronsted superacid. The reaction proceeds through O,C-diprotonated forms of starting allenes, as confirmed by experimental and theoretical investigations.
Article
Chemistry, Multidisciplinary
Yuliya V. Zhelonkina, Olesya V. Khoroshilova, Alexander Yu. Ivanov, Irina A. Boyarskaya, Vasilii V. Pelipko, Sergey V. Makarenko, Aleksander V. Vasilyev
Summary: Methyl or ethyl 3-nitropropenoates react with arenes in triflic acid tetrahydrofuran solution to form oximes of alkyl 2,3-diaryl-3-oxopropanoates in good yields. The obtained oximes exhibit atropoisomerism due to the presence of ortho-methyl substituents in the aryl ring. The reactive electrophiles in this reaction are AlkO(HO+)C1-C2H=C3H-N+(O)(OH) species protosolvated on the NO2 and CO2R acceptor groups.
Article
Chemistry, Multidisciplinary
Olesya V. Khoroshilova, Kristina E. Borovkova, Lia R. Nikiforova, Julia V. Salmova, Artem O. Taraskin, Daria V. Spiridonova, Aleksander V. Vasilyev
Summary: Trimethylsilyl ethers of trifluoromethyl substituted benzyl type alcohols of thiophene and (benzo)furan series undergo multichannel electrophilic transformations in triflic acid CF3SO3H (TfOH), leading to the formation of various products.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matvei A. Kochurin, Alina R. Ismagilova, Dmitriy N. Zakusilo, Olesya Khoroshilova, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: Reactions of compounds with linear conjugated dienone structures with arenes under superelectrophilic activation conditions result in the formation of various compounds. The formation of the reaction products depends on the structures of the starting compounds and the reaction conditions. The starting dienones act as precursors of electrophilic synthesis intermediates, leading to the formation of target products.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ivan A. Shershnev, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: By studying the reaction mechanism of 5,5,5-trichloropent-3-en-2-one in Bronsted superacid CF3SO3H, it was found that a novel class of indene derivatives can be formed.
