Article
Chemistry, Organic
Yichun Wang, Deyang Jia, Jing Zeng, Yuming Liu, Xiubin Bu, Xiaobo Yang
Summary: A visible-light-accelerated Rh(III)-catalyzed C-H annulation of aromatic amines with bicyclic alkenes was developed for the synthesis of benzocarbazole derivatives. The reaction proceeded smoothly at room temperature, delivering good to excellent yields of bridged oxa or aza tetrahydro benzocarbazoles. Furthermore, benzo[b]carbazoles were conveniently synthesized through further aromatization in one pot, showcasing the method's potential for various applications.
Article
Chemistry, Organic
Narasingan Aravindan, Masilamani Jeganmohan
Summary: A new synthetic methodology efficiently prepared biologically important benzophenanthridines in three steps. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional groups to synthesize the target molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Rohit Sarthi, Rohit Kumar, Tamanna Sharma, Upendra Sharma
Summary: In this study, a concise Rh(III)-catalyzed C(sp3)-H alkylation of 8-methylquinolines with oxabenzonorbornadiene scaffolds and other strained olefins was presented. The developed catalytic methodology exhibits key features such as the retention of the oxabenzonorbornadiene skeleton, broad substrate scope, and wide-ranging functional group tolerance. Mechanistic studies revealed that the reaction proceeds through a non-radical pathway, with the five membered rhodacycle serving as the key intermediate. This is the first report on the C(sp3)-H alkylation of 8-methylquinolines with strained oxabenzonorbornadiene scaffolds (with ring retention).
Article
Chemistry, Organic
Giulia Mazzoccanti, Roberta Franzini, Alessia Ciogli, Marco Pierini, Fabio Buonsenso, Cristina Faggi, Antonio Francioso, Simone Manetto, Claudio Villani
Summary: This study investigates the chirality of dibenzocyclooctynes through theoretical and experimental methods. Computational analysis is conducted and used as a guide for experimental investigation. An array of different experiments is then used to elucidate the structure, including HPLC, chiroptical spectroscopy, and X-ray diffraction. The study demonstrates the chirality and conformational behavior of dibenzocyclooctynes and their derivatives with azides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zepeng Zhang, Yunpeng Gao, Shufeng Chen, Jianbo Wang
Summary: This study demonstrates a living/controlled vinyl addition polymerization of 3-methyl-3-carboxymethyl cyclopropenes catalyzed by [Pd(pi-allyl)Cl](2) ligated by a sulfinamide bisphosphine ligand, showing linear increase in number-average molecular weight (Mn) with the initial feed ratio of monomer to catalyst and successful controlled block copolymerization via sequential monomer addition. The synergistic coordination action of the catalyst ligand and the lateral carbonyl group in the cyclopropene moiety plays a key role in achieving efficient polymerization in a living/controlled manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Maximilian P. Mueller, Alexander Hinz
Summary: Silacycles are widely used building blocks in organic synthesis. In this study, small silacycles were expanded catalytically to form larger cyclic compounds. The reactivity and reaction mechanisms of these silacycles were investigated, showing that they can undergo ring expansion reactions and subsequent isomerization reactions. This research provides insights into the reactivity patterns of silacycles and their potential applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jingjing He, Chuan Liu, Yupian Deng, Qianding Zeng, Yi Zhang, Ying Liu, Pai Zheng, Song Cao
Summary: A mild and efficient DBN-mediated addition reaction was developed for the synthesis of various β-trifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines using α-(trifluoromethyl)styrenes and diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines.
Article
Chemistry, Organic
Baihui Zheng, Xiaotong Li, Yang Song, Shuyang Meng, Yifei Li, Qun Liu, Ling Pan
Summary: A visible-light-induced [3+2] oxidative cyclization of alkynes with ketene dithioacetals in the presence of an acridine photosensitizer was reported, leading to regioselective synthesis of multisubstituted thiophenes in high yields under metal-free conditions. This reaction showed good substrate tolerance and efficiency in large-scale syntheses. The reaction mechanism and applications were detailed to illustrate the reactivity of the new 1,3-dipoles and the selectivity of the reactions.
Article
Chemistry, Organic
Linpeng Liu, Yanyu Jian, Weigao Hu, Shaohu Zhao, Zhang-Jie Shi, Nicklas Selander, Taigang Zhou
Summary: A method for radical cyclization and ring-opening of oxime esters with diselenides has been developed. Both Ni(0) and Fe(ii) catalysts can be used for the selenylation of olefin-containing and cyclic oxime ester derivatives. Using this method, a variety of functionalized pyrrolines and alkyl nitriles can be synthesized in good yields. Additionally, a mechanism involving iminyl radical and carbon-centered radical intermediates has been proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jin-Feng Lv, Yu-Fang Tan, Ya-Nan Zhao, Dan Yang, Yan-Hong He, Zhi Guan
Summary: The paper describes an electrochemical method for the synthesis of N-vinyl benzotriazoles by coupling olefins with benzotriazoles to form C(sp(2))-N bonds. It is a highly atom-economic and clean reaction, with nBu4NI serving as both an electrolyte and an iodine mediator, and hydrogen as the only byproduct.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Austin Pounder, Leanne D. Chen, William Tam
Summary: The ruthenium-catalyzed [2 + 2] and homo Diels-Alder [2 + 2 + 2] cycloadditions of norbornadiene with disubstituted alkynes were investigated using density functional theory (DFT), providing mechanistic explanations for reactivity trends with different functional groups. Computational studies revealed distinct mechanistic pathways for the [2 + 2 + 2] cycloaddition, with Cp*RuCI(COD) energetically preferring the cationic pathway, and showed that the rate-determining step for the [2 + 2] cycloaddition is the final reductive elimination step.
Article
Chemistry, Organic
Yun-Xuan Tan, Xing-Yu Liu, Cheng-Yu He, Ping Tian
Summary: This study presents a Rh(III)-catalyzed asymmetric carboboration of heterobicyclic alkenes, including 7-oxa- and 7-azabenzonorbornadienes, achieving the transformation with high yields and excellent enantioselectivities. The product bearing seven chiral centers was efficiently obtained, and several transformations of the carboboration product were also demonstrated.
Article
Chemistry, Organic
Liu Shi, Qiang Xiong, Shu-Yi Wu, Yang Li, Peng Shen, Ji Lu, Guang-Yao Ran
Summary: Novel cyclic vinylogous anhydrides were designed and utilized as five-carbon carbonyl synthons for [5 + 5] annulation with vinylethylene carbonates under chiral palladium catalysis. The strategy exhibited excellent regioselectivity, mild conditions, and broad substrate scope, leading to the synthesis of spiro ten-membered lactones bearing oxindole and pyrrolidinone motif in high yield (up to 99%) with moderate to high enantioselectivity (up to 89% ee).
Article
Multidisciplinary Sciences
Kelvin Pak Shing Cheung, Jian Fang, Kallol Mukherjee, Andranik Mihranyan, Vladimir Gevorgyan
Summary: Aliphatic allylic amines are complex and biorelevant molecules that are present in a wide range of compounds. The direct allylic C-H amination of alkenes is the simplest method to obtain these motifs. However, using widely available internal alkenes with aliphatic amines remains a synthetic challenge. We report a general solution to these problems using a blue light-induced open-shell approach and a mild oxidant.
Article
Chemistry, Applied
Xiao Hu, Minglin Tao, Zhongxiao Ma, Yi Zhang, Yanni Li, Deqiang Liang
Summary: A novel reaction method is proposed in this study, which enables regioselective tandem enamido beta-C(sp(2))-H alkylation/acrylamido alkylation/cyclizative alkenylation sequence of 3-aza-1,5-dienes under visible light irradiation. This method shows excellent regiospecificity and broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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.
