Article
Chemistry, Organic
Yan Chen, Andrey Shatskiy, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported in this study, providing access to various synthetically useful N-fused heterocyclic scaffolds. The mechanism involves nucleophilic addition/protonation/elimination/cydoisomerization pathways. The protocol established in this research is controlled, facile, and modular.
Article
Chemistry, Multidisciplinary
Jan Toenjes, Lars Longwitz, Thomas Werner
Summary: A catalytic, base-free Wittig reaction has been developed using PMHS as a terminal reductant, which allows for low catalyst loadings and compatibility with various functional groups. The system exhibits high stereoselectivity and yields up to 96%, making it a promising method for the synthesis of highly functionalized alkenes.
Article
Chemistry, Applied
Seungwon Lee, Mohamed Ahmed Abozeid, Hun Young Kim, Kyungsoo Oh
Summary: A Cu(OTf)(2)-catalyzed olefination of cyclohexadienones using sulfonylmethyl isocyanides was developed. The presence of a CF3 moiety at the 4-position of cyclohexadienones promoted the formation of olefination products through a preferential [3+2] cycloaddition with the ketone moiety and a facile fragmentation of transient oxazoline intermediates. This study elucidated the reaction dichotomy of olefination of 4-CF3-substituted cyclohexadienones, involving a CF3-controlled 1,2-addition pathway and a Van Leusen 1,4-addition pathway through the electrostatic repulsion effect.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yingying Shan, Lei Su, Dianpeng Chen, Min Yang, Wenlin Xie, Guanyinsheng Qiu
Summary: In this study, a palladium-catalyzed [4+1] cycloaddition reaction was developed for the synthesis of a series of 2-amino-4-cyanofurans and 2-amino-4-amidylpyrroles with high efficiency and broad reaction scope. Mechanism studies suggest that the palladium-catalyzed [4 + 1] imidoylative cycloaddition of prop-2-yn-1-ones was concerted. This work provides a potential strategy for the synthesis of valuable heterocyclic compounds.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Applied
Naveenkumar Anugu, Sanjeeva Thunga, Sivaparwathi Golla, Hari Prasad Kokatla
Summary: A new regioselective method has been developed for the insertion of isocyanide into the C2-H position of quinoline N-oxides catalyzed by molecular iodine, resulting in rapid access to quinoline 2-formamides with exceptional functional group tolerance, broad substrate scope, and 100% atom-economy. This metal-free reaction has synthesized a library of 33 N-(2-quinolinyl)formamides, which may have potential applications in pharmaceuticals and synthetic chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Metallurgy & Metallurgical Engineering
Ilker Kara
Summary: The study investigated the effects of adding different proportions of reductant materials and varying reaction temperatures on the properties of composite pellet samples, showing that pellets produced with 3% sodium bentonite at 1100 degrees C exhibited the highest compressive strength and metallization rate.
JOURNAL OF CENTRAL SOUTH UNIVERSITY
(2021)
Article
Chemistry, Organic
Lianhong Jiao, Yanan Wang, Lixia Ding, Chaofeng Zhang, Xiao-Na Wang, Junbiao Chang
Summary: A novel metal-free annulation of ynamides with 2H-azirines catalyzed by BF3·Et2O is described, leading to the construction of polysubstituted 2-aminopyrroles in a facile, flexible, and atom-economical way. This synthetic strategy proceeds with efficiency, broad substrate scope, and short reaction time under mild reaction conditions. Furthermore, the obtained annulation products could be modified to generate diverse 2-iminopyrrole frameworks in high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Huaxin Lin, Senling Tang, Yang Pan, Peng Liang, Xiaofeng Ma, Wei Jiao, Huawu Shao
Summary: A new method for the synthesis of 2-aminobenzofurans using Sc(OTf)(3) has been described, utilizing o-QMs as intermediates and providing a straightforward and efficient approach for the construction of the scaffold.
Article
Chemistry, Multidisciplinary
Jin Wang, Zhaoyang Li, Shengxin Bai, Qinghua Zhou, Tengteng Wu, Zhongyan Hu, Xianxiu Xu
Summary: This study presents an unprecedented [4 + 3] cycloaddition of furoketenimines with furocarbenoids for the efficient synthesis of cycloheptafuran and cycloheptapyrrole scaffolds. Zinc chloride acts as a promoter to form transient intermediates from isocyanides and ene-yne-ketones, and subsequently constructs a seven-membered ring. This three-component one-pot domino reaction sequentially constructs three rings and five bonds.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Kamran Amiri, Behrouz Nayebzadeh, Mohammad Kamangar, Mohammad Babazadeh, Alireza Ariafard, Farshad Shiri, Frank Rominger, Saeed Balalaie
Summary: A new green synthetic protocol for constructing a variety of substituted fused azabicyclo[3.3.1]nonadiquinoline scaffolds has been presented. This unified strategy offers a wide substrate scope and high functional group tolerance, leading to good to high yields under environmentally friendly, transition-metal-free, low-cost, and operationally simple conditions. The proposed method outperforms existing methods in terms of green and sustainable conditions. The reaction mechanism has been confirmed using DFT calculations.
Article
Chemistry, Multidisciplinary
Tamal Kanti Das, Agustin M. Rodriguez Trevino, Sanjay Pandiri, Sini Irvankoski, Juha H. Siitonen, Sara M. Rodriguez, Muhammed Yousufuddin, Laszlo Kurti
Summary: Both metal-catalyzed and organocatalytic transfer hydrogenation reactions are commonly used for reducing C=O and C=N bonds, but achieving selectivity in transfer hydrogenation of C=C bonds remains challenging. This article presents an unconventional catalyst-free transfer hydrogenation reaction of activated alkenes using isopropanol as a green reductant and solvent. The reaction provides a convenient method to access a variety of substituted malonic acid half oxyesters (SMAHOs) in moderate to good yields, and mechanistic studies suggest an unprecedented hydrogen bond-assisted transfer hydrogenation process.
Article
Chemistry, Multidisciplinary
Yan Wu, Jin-Yang Chen, Jing Ning, Xue Jiang, Jie Deng, Yu Deng, Rui Xu, Wei-Min He
Summary: An electrochemical multicomponent reaction was developed for the construction of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions, providing a green and straightforward protocol. A variety of 4-selanylpyrazole derivatives were synthesized from readily available raw materials with good to excellent yields.
Article
Chemistry, Organic
Hongliang Shi, Huachen Hou, Jinbo Duan, Jinwei Huang, Xiaoguang Duan, Xingang Xie, Huilin Li, Xuegong She
Summary: The total syntheses of Lycopodium alkaloids phleghenrines A and C have been achieved in 19 and 18 steps, respectively, using three (hetero)-Diels-Alder reactions and two ring-expansion reactions. A chiral precursor is prepared through an auxiliary controlled Diels-Alder reaction, enabling asymmetric synthesis. This strategy offers a general approach to synthesizing novel Lycopodium alkaloids.
Article
Chemistry, Organic
Muhua Wang, Linghua Zhang, Xi Chen, Xinying Zhang, Xuesen Fan
Summary: A novel synthesis of pyrazolidinone fused 1,3-benzooxazepine derivatives via a formal [4 + 3] annulation reaction of 1-phenylpyrazolidinones with diazonaphthalen-2(1H)-ones is presented. The mechanism involves an unprecedented reaction mode of 1-phenylpyrazolidinone, featuring cascade C-alkylation/C-annulation through C(sp(2))-H/C(sp(3))-H bond cleavage. Compared with literature methods, this protocol offers advantages such as easily accessible starting materials, structurally complex and biologically attractive products, a unique mechanistic pathway, and excellent chemo/regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yue Sun, Zuguang Yang, Shu-Ning Lu, Zhengkai Chen, Xiao-Feng Wu
Summary: A straightforward strategy for the metal-free construction of trifluoromethyl-containing pyrazole derivatives has been achieved. The protocol features mild conditions, easy operation, excellent substrate compatibility, and good regioselectivity. The utility of this method is demonstrated through scale-up reaction and further elaboration of the obtained pyrazole products.
Article
Chemistry, Multidisciplinary
Lou Shi, Mingshan Wang, Ling Pan, Yifei Li, Qun Liu
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Chengjie Feng, Yifei Li, Qi Xu, Ling Pan, Qun Liu, Xianxiu Xu
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Chengjie Feng, Yifei Li, Xinyao Sheng, Ling Pan, Qun Liu
Article
Chemistry, Organic
Mingshan Wang, Lou Shi, Yifei Li, Qun Liu, Ling Pan
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Qi Xu, Baihui Zheng, Xiaoxuan Zhou, Ling Pan, Qun Liu, Yifei Li
Article
Chemistry, Organic
Xiaohui Yang, Baihui Zheng, Yanqing Wang, Yifei Li, Qun Liu, Ling Pan
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
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
Qi Xu, Xiaoxuan Zhou, Si Zhang, Ling Pan, Qun Liu, Yifei Li
Summary: The sulfur-alkenylation reaction described is a highly selective process that can be induced by visible light, making it applicable to a wide range of alkene substrates. This method is also useful for late-stage functionalization of natural products and complex molecules.
Article
Chemistry, Organic
Baihui Zheng, Xiaotong Li, Shuyang Meng, Yifei Li, Qun Liu, Ling Pan
Summary: The development and applications of novel synthetic intermediates play a crucial role in synthetic chemistry. alpha-Amino alkyl radicals show promise as synthetic intermediates for the construction of versatile natural products and drugs. However, their applications have been limited due to the high reduction potentials of imines and further oxidation of the generated alpha-amino alkyl radicals. In this study, we demonstrate the selective generation of p-(N,N-dimethyl)benzyl equivalents from easily-available N,N-dimethyl arylamines via alpha-amino alkyl radicals in the presence of an iridium photosensitizer, without the need for any other additives. Under mild reaction conditions, a series of trifluoromethyl-containing diarylalkanes were obtained in good to high yields from the visible-light-promoted reaction of N,N-dimethyl arylamines and quinols. This route provides a novel and environmentally-friendly method for accessing trifluoromethyl-containing arenes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yang Song, Baihui Zheng, Shuo Yang, Yifei Li, Qun Liu, Ling Pan
Summary: A novel trifluoromethylation method using trifluoroacetic anhydride (TFAA) as the CF3 source under photoredox catalysis is developed. The reaction shows excellent tolerance, even on a gram scale, and can be applied to natural products and prodrugs. This simple protocol provides a practical utilization of TFAA and also enables perfluoroalkylations and trifluoromethylation/cyclizations under identical conditions.
