Review
Chemistry, Multidisciplinary
Raj Kamal, Omkar, Vipan Kumar, Rajesh Kumar
Summary: Organo hypervalent iodine reagents have become attractive and versatile reagents for various chemical transformations in synthetic organic chemistry. They are milder and exhibit similar reactivity compared to toxic heavy metal reagents. Hydroxy(tosyloxy)iodobenzene, also known as Koser's reagent, is used as an environmentally sustainable alternative and has successfully contributed to the synthesis of important heterocycles.
Article
Chemistry, Organic
Guanyu Wang, Dongchang Han, Yue Li, Yangleiyu Nie, Selvaraj Muthusamy, Zhibin Luo, Bin Liu
Summary: The deconstructive ring cleavage of cyclic thioethers is achieved using boron compounds. The sequential hydroboration/ring cleavage process enables the preparation of vinyl sulfides via newly developed conditions. Further exploration demonstrates the versatility of nucleophiles, leading to various functionalized sulfides with linear frameworks.
Article
Chemistry, Multidisciplinary
Junwei Zheng, Linli Zhang, Chaoren Shen, Kaiwu Dong
Summary: The study introduces a method for cobalt-catalyzed carbonylative ring expansion of thietane under ambient CO pressure, showcasing the dual roles of Co-2(CO)(8) as a precursor for both carbonylation catalyst and Lewis acid. Additionally, the carbonylative ring expansion was successfully demonstrated under CO gas-free conditions using Co-2(CO)(8) as both a CO surrogate and pre-catalyst.
Article
Chemistry, Multidisciplinary
Paolo Piacentini, Tanner W. Bingham, David Sarlah
Summary: In this study, a concise method for the preparation of benzocycloheptenes from non-activated polycyclic arenes is reported, providing an alternative to the Buchner reaction. This methylene-insertion molecular editing approach enables rapid conversion of (hetero)arenes into substituted (aza)benzocycloheptatrienes, which can undergo various functionalizations downstream.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Wen-Jing Yan, Hai-Yong Tu, Zhiyong Liao, Xiao-Qin Shen, Xing-Guo Zhang
Summary: A method for constructing the indane skeleton was described, involving a palladium-catalyzed ring-opening diarylation of Cyclobutanols with aryl 1,2-dihalides. The reaction proceeds through beta-carbon elimination and subsequent alpha-carbon arylation of ketone, resulting in the formation of 2-acylindanes in yields of 42-93%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Chih-Wei Hsu, Yen-Ting Lu, Chi-Ping Lin, Woo-Jin Yoo
Summary: A synthetic strategy involving Simmons-Smith cyclopropanation and acid-catalyzed pinacol rearrangement was developed to transform α-hydroxy silyl enol ethers into 1-substituted bicyclo[2.1.1]hexan-5-ones. These bicyclic ketones underwent further synthetic manipulations to generate various 1,5-disubstituted bicyclo[2.1.1]hexanes, which could serve as potential bioisosteres of ortho-substituted arenes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Tiffany O. Paulisch, Lukas A. Mai, Felix Strieth-Kalthoff, Michael J. James, Christian Henkel, Dirk M. Guldi, Frank Glorius
Summary: In this research, a photocatalyzed two-carbon ring expansion of beta-dicarbonyl compounds with unactivated olefins was achieved, facilitated by selective sensitization of the substoichiometric enol tautomer and the identification of a metal-based sensitizer fac-[Ir(CF3-pmb)(3)]. This sensitizer proved effective in facilitating the reaction, allowing for the synthesis of medium-sized rings in organic compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Song Zou, Zeyu Zhang, Chao Chen, Chanjuan Xi
Summary: This study achieved the formal [4 + 2] annulation of styrene oxides with alkynes catalyzed by MeOTf, resulting in polysubstituted naphthalenes with sequential electrophilic cyclization/ring expansion. The reaction showed high regioselectivity with satisfactory yields and could be carried out on gram scale.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Ksenia Lavit, Alexander Sapegin, Stanislav Linnik, Mikhail Ryazantsev, Mikhail Krasavin
Summary: The influence of introducing substituents of increasing bulk in the alpha position of tetracyclic imidazoline-fused heteroazepinones on the course of hydrated imidazoline ring expansion (HIRE) reaction has been established.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Xinyuan Zhang, Li Lin, Jing Li, Shiyu Duan, Yuhang Long, Jiahong Li
Summary: Medium-sized rings and macrocycles, which are crucial components in drugs and natural products, have attracted significant attention from chemists in developing simple, green, and efficient synthesis methods. Recent advancements in ring expansion/cyclization reactions for these compounds have been reviewed to outline the future prospects and development in this field.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Agriculture, Multidisciplinary
Miyo Tanaka, Hisashi Nishiwaki, Satoshi Yamauchi
Summary: A novel tri-substituted tetrahydropyran type 8,7'-neolignan and its enantiomer with higher enantiomeric excess were synthesized from all cis-tetra-substituted tetrahydrofuran with an iodomethyl group. The phytotoxicities of the synthesized compounds were compared to find the most phytotoxic tri-substituted tetrahydropyran type 8,7'-neolignan.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Applied
Yuya Miki, Naohito Tomita, Kazuho Ban, Hironao Sajiki, Yoshinari Sawama
Summary: An efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions is reported. The reaction generates nitrogen as the sole by-product and the 1-pyrrolines can be further transformed into other compounds in one-pot manner.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Thuy Quynh Le, Niaz Liaba, Da In Jeong, Jeonghyo Lee, Chang Ho Oh
Summary: Here, we present an efficient synthetic method for preparing [6-7-6]-icetexane derivatives. This method utilizes a copper-catalyzed intramolecular cyclization and a subsequent ring expansion protocol to generate the desired [6-7-6] scaffold. The approach demonstrates high efficiency and versatility, allowing for the synthesis of icetexane compounds with diverse functional groups.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Wenhao Yuan, Jiaxi Xu
Summary: Oxetanes are important small heterocycles widely used in organic, pharmaceutical, and polymer chemistry, with a preference for ring-opening and ring expansion reactions to construct various oxygen-containing large heterocyclic compounds. This review discusses the different ring expansion reactions of oxetanes and their reaction mechanisms, while also proposing new prospects for future development.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Davit Hayrapetyan, Lyailya Yussupova, Almaz Kaipov, Aigerim Galyamova
Summary: The simple and scalable electrochemical oxidation of the electron-rich benzene ring, followed by intramolecular capture of reactive cation-radical intermediates, enables the synthesis of spirocyclic morpholines and tetrahydrofurans. The obtained molecules can be easily modified into valuable building blocks.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
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.