Article
Chemistry, Organic
Alessandra Casnati, Dawid Lichosyt, Bruno Lainer, Lukas Veth, Pawel Dydio
Summary: The research presents a multicatalytic method for converting alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivity. Prochiral allylic alcohols can also be selectively transformed into different stereoisomers of the product.
Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guang Chen, Yue Wang, Jie Zhao, Xinying Zhang, Xuesen Fan
Summary: A one-pot cascade reaction of o-alkynylnitrobenzenes with maleimides was successfully achieved under Au(III)- Cu(II) relay/synergetic catalysis, leading to the formation of hydroxysuccinimide substituted indolin-3-ones. The reaction showed good atom economy, compatibility with a wide range of substrates bearing various functional groups, and significant antiproliferative activity in human cancer cell lines for the obtained products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Liang-Hua Zou, Biao Liu, Cheng Wang, Zeyu Shao, Junqi Zhou, Andong Shao, Jian Wen
Summary: An efficient and green method for synthesizing various alkyl amines through the cleavage of vinylsulfonium salts' C(sp(3))-S bond has been developed. This reaction can be conducted under air atmosphere and shows a broad range of applicability with N-nucleophiles. Additionally, N-vinylazoles can be obtained with moderate to good yields through the reaction of vinylsulfonium salts with N-containing heterocycles in the presence of a base at room temperature.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Nicolai A. Aksenov, Alexander V. Aksenov, Igor A. Kurenkov, Nikita K. Kirillov, Dmitrii A. Aksenov, Nikolai A. Arutiunov, Daria S. Aksenova, Michael Rubin
Summary: A highly efficient one-pot method for the synthesis of biologically active 2-(3-oxoindolin-2-yl)acetonitriles has been designed, which involves a base-assisted aldol reaction followed by hydrocyanation, triggering an unusual reductive cyclization reaction.
Article
Chemistry, Organic
Letian Zhang, Jiajun He, Jiabin Shen, Hao Xu, Dancheng Zhu, Chao Shen
Summary: A one-pot stepwise Ce(III)/photoassisted cross-dehydrogenative coupling/fluorooxidation process was developed to efficiently construct C3-heteroaryl 3-fluorooxindoles. This method utilized readily available chemical feedstocks and did not require the use of precious metals, oxidants, or additives. The products were obtained in moderate-to-good yields through recrystallization with favorable functional group compatibility. Additionally, this methodology successfully established C-C, C=O, and C-F bonds in a single step, providing a direct transformation of C=C bonds to functionalized C-C bonds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Grigorii K. Sterligov, Alexandra A. Ageshina, Sergey A. Rzhevskiy, Olga V. Shurupova, Maxim A. Topchiy, Lidiya I. Minaeva, Andrey F. Asachenko
Summary: This research article presents a one-pot, two-step procedure for the synthesis of 1,2-disubstituted-3-tosyl and 1,2-disubstituted-3-cyanoindoles from N-(o-tolyl)benzamides. The developed procedure is operationally simple, does not require any transition metals, and provides variously substituted indoles in good yields from readily available starting materials.
Article
Chemistry, Organic
Timothy J. McClure, Connor Saludares, Gisela Martinez, Cheyenne Orozco, Raul Navarro
Summary: A new family of stabilized benzylic nucleophiles has been developed for the palladium-catalyzed decarboxylative allylic alkylation reaction, which can efficiently synthesize a variety of functionalized phthalides under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bumpei Maeda, Yusuke Aihara, Ayato Sato, Toshinori Kinoshita, Kei Murakami
Summary: This article describes a photoinduced benzylic C-H thiocyanation method. A series of alkyl thiocyanates were efficiently synthesized using Selectfluor as the oxidant, and one-pot isothiocyanation was achieved following the C-H thiocyanation. The resulting thiocyanates and isothiocyanates can be applied to the divergent transformation of pharmaceuticals.
Article
Chemistry, Multidisciplinary
Luca C. C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: In this study, phenyl azides substituted by an (alkylphenyl)ethynyl group were found to facilitate benzylic sp(3)(C-H) functionalization under the presence of a JohnPhosAu catalyst, resulting in the synthesis of indole-fused tetra- and pentacycles through divergent N- or C-cyclization. The chemoselectivity of the reaction was found to be influenced by the counter-anion, the electron density of the alpha-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Majji Shankar, Arijit Saha, Arghadip Ghosh, Somratan Sau, Akhila K. Sahoo
Summary: In this study, the sulfur and nitrogen moieties of methylphenyl sulfoximine (MPS)-enabled aryl thioamides were independently involved in annulation with unactivated alkynes to construct unusual 6,6-fused thiopyranoisoquinoline skeletons. The innovative Ru-catalyzed one-pot double annulation of aryl thioamides with alkynes was achieved through overcoming challenges such as the S poisoning effect and susceptibility of S to oxidation. The novel isothiochromene-1-one skeletons were successfully constructed, initiating the annulation with S preference over the N motif of thioamides with alkynes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kazumasa Tanimoto, Hayaki Okai, Marina Oka, Ryoma Ohkado, Hiroki Iida
Summary: The aerobic oxidative cross-coupling of indoles with azoles is developed using flavin-iodine-coupled organocatalysis for the green synthesis of 2-(azol-1-yl)indoles. The one-pot three-component synthesis of 2-azolyl-3-thioindoles is achieved in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.
Article
Chemistry, Organic
Zhi-Cheng Yu, You Zhou, Xiang-Long Chen, Jin-Tian Ma, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
Summary: A reductive coupling reaction was established for the synthesis of diaryl 1,2-dicarbonyl compounds from aryl methyl ketones. The reaction involves C(CO)-C(sp3) bond cleavage and proceeds through an electron transfer process. Notably, this reaction is simple to operate, has mild reaction conditions, and is applicable to a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nandkishor Prakash Khot, Nitish Kumar Deo, Manmohan Kapur
Summary: In this study, a novel vinylogous reactivity of vinyl diazo esters in the C-H bond allylation of benzamides has been developed by combining cobalt and photoredox catalysis. The key factor for the success of this reaction is the close interaction between the high valent cobalt catalyst and the photocatalyst. The reaction utilizes oxygen as the sole oxidant and only generates benign nitrogen as a by-product. It demonstrates a broad substrate scope for both vinyl diazo esters and benzamides.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hemanta Hazarika, Kangkana Chutia, Babulal Das, Pranjal Gogoi
Summary: An aryne-based synthetic protocol has been developed for the synthesis of 3-substituted-3-hydroxy-indolin-2-ones, yielding a wide variety of products in good yields. One of the synthesized compounds has been confirmed by single crystal XRD analysis. Treating the synthesized derivatives with an inorganic base at high temperature leads to an interesting o-arylated product of 1,3-cyclohexandione.
NEW JOURNAL OF CHEMISTRY
(2021)
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.