Article
Chemistry, Applied
Guorong Xiao, Kaifu Wu, Wei Zhou, Qian Cai
Summary: A copper-catalyzed [3+2] cylcoaddition/ alkenyl C-N coupling tandem reaction was demonstrated, providing a method for the formation of triazolopiperidine skeletons.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Summary: A stereospecific three-component domino reaction was revealed under catalyst-free conditions, leading to the synthesis of a wide range of benzothiophene-fused polycycles and eight-membered N-heterocycles. The control over product formation was achieved by regulating the stereoconfiguration of cyclohexane-1,2-diamines. The detailed mechanism and origin of the chemoselectivity were explored using density functional calculations, revealing the influence of intramolecular attractions and steric effects on the observed chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Cong Zhang, Yuhang He, Guanghui An
Summary: Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes have been developed. By switching the substituent site at the C2 and C4 positions of quinolines, either C2 Minisci alkylation or C4 reductive alkylation could be achieved. These approaches feature mild conditions and sensitive functional group tolerance, which enables the functionalization of natural products and medicines. Mechanism investigation revealed that Fe(dibm)(3) would be a dual promoter for both alkyl radical transfer and generation of the more reactive hydrogen donor Ph(RO)SiH2.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Valentina Pelliccioli, Davide Dova, Clara Baldoli, Claudia Graiff, Emanuela Licandro, Silvia Cauteruccio
Summary: Efficient and versatile synthetic routes to functionalized tetrathia[7]helicenes (7-THs) have been described in this study. Key intermediates were synthesized using palladium-catalyzed homocoupling reactions and annulation reactions. The versatility of bromides 1 for preparing a variety of 7-TH derivatives, including 7,8-disubstituted and 7-monosubstituted compounds, has been demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Remi Lavernhe, Ruben O. Torres-Ochoa, Qian Wang, Jieping Zhu
Summary: A versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes has been developed, leading to the synthesis of medicinally important heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla
Summary: The participation of reactants in polarity inversion allows the continuation of productive domino processes in multicomponent reactions, leading to the discovery of novel reaction pathways and various polyheterocyclic scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Article
Chemistry, Multidisciplinary
Chao Jiang, Pinhong Chen, Guosheng Liu
Summary: In this study, a novel reaction technique combining photocatalysis and copper catalysis was developed for the radical decarboxylative C(sp(3))-C(sp(3)) cross-coupling of NHPI esters and cyclopropanols, leading to the efficient synthesis of ss-benzyl ketones. The terpyridin-4'-one ligand played a vital role in the reaction by facilitating the capture of benzylic radicals by alkyl-copper species generated through the copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing a new approach for C(sp3)-C(sp3) bond formation.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qian Pu, Mingming Huo, Guojuan Liang, Lijuan Bai, Genhui Chen, Hongjiao Li, Peng Xiang, Hui Zhou, Jing Zhou
Summary: Highly selective divergent oxidative dearomatization coupling reactions have been reported, where the chemoselectivity is controlled by catalysts and bases. Three different kinds of polycyclic cyclohexadienones are generated from the same reactants (41 examples, 85-99% yield). This method represents a novel copper- and palladium-catalyzed C-H oxidative dearomatization of phenolic derivatives.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Masashi Yokoya, Takaaki Ishiguro, Yoshiaki Sakairi, Shinya Kimura, Yuji Morita, Masamichi Yamanaka
Summary: A novel and efficient method for synthesizing benzo[de]chromene-7,8-dione derivatives without post-oxidation of benzo[de]chromenes was developed. The synthesized compounds exhibited strong antimicrobial activity, particularly against multidrug efflux pump-deficient strains.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Leiqing Fu, Jie-Ping Wan, Liyun Zhou, Yunyun Liu
Summary: In this study, a copper-catalyzed annulation of enaminones with alkynyl esters was developed for the synthesis of different pyrroles with a 2,3,4,5-tetrasubstituted structure. By using Cu(OAc)(2) as the catalyst, the synthesis of 2-vinyl and 2,3-dicarboxyl-functionalized pyrroles was achieved using terminal and internal alkynyl esters, respectively. The synthesis of 2-vinyl pyrroles represents the first example of accessing 2-vinyl substituted pyrroles via direct cascade reactions involving vinylation and pyrrole ring formation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Fayun Chen, Li-Xia Quan, Anxi Zhou, Congbin Ji, Yanhong Li, Xianhong Zhu, Liu-Liang Mao, Jie-Ping Wan
Summary: An efficient and facile strategy was developed for the synthesis of 6-(sulfonylmethyl)phenanthridines and its derivatives through tandem sulfonylation cyclization of vinyl azides. The reaction utilizes accessible and cheap K2S2O5 as the sulfur dioxide source and achieves moderate to excellent yields with easy operation and gram-scale synthesis, as well as good functional-group tolerance.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liu-Liang Mao, Li-Xia Quan, Yunyun Liu, Jie-Ping Wan
Summary: Nitrogenous heterocyclic compounds are important building blocks and intermediates in synthetic chemistry. The construction of these compounds in aqueous mediums has been a notable research topic due to its sustainability and the replacement of volatile organic solvents with water. This article highlights recent advancements in the synthesis of nitrogen heterocycles in aqueous mediums over the past two years.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Organic
Huan Gao, Liyun Zhou, Jie-Ping Wan, Yunyun Liu
Summary: Rongalite has been used as a cheap and efficient carbonsynthonfor the synthesis of divergent N-heteroaromatics, including differentpyridines and quinolines. The selective synthesis of different productscan be achieved by employing enaminones or enaminones/anilines asreaction partners. Rongalite displays an evident advantage in providing products with considerably higher product yields under milder conditions compared with the reaction using conventional aldehyde synthons. The GC-MS analysis of the reaction process has been performed to probe the possible reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shanghui Tian, Yunyun Liu, Changfeng Wan, Jie-Ping Wan, Guifeng Hao
Summary: A simple and efficient method for synthesizing cinnolines is developed by reacting readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions produce diversified cinnolines without the need for catalysts or additives by heating in dimethyl sulfoxide. Furthermore, the investigation of their anti-inflammatory activity reveals promising candidates, p-chlorobenzoyl (3f) and p-nitrobenzoyl (3j) cinnolines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Liyun Zhou, Chengping Wen, Jie-Ping Wan
Summary: By using readily available enaminones, aryl hydrazine hydrochlorides, and alkynes, a chemo-selective three-component synthesis of atropisomeric N-(o-alkenylaryl)pyrazoles was efficiently achieved with rhodium catalysis. Unlike the Satoh-Miura reaction, which uses pre-prepared N-phenyl pyrazoles and alkynes as substrates for alkyne-based C-H benzannulation, this three-component protocol demonstrates unprecedented selectivity of C-H alkenylation by blocking the second round metal alkenylation with the key protonation step in the presence of acids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Lin, Jie-Ping Wan, Yunyun Liu
Summary: This article describes a facile cascade reaction for the site-selective synthesis of 2-cyanochromones. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials, and I2/AlCl3 as promoters, the products are obtained through tandem chromone ring formation and C-H cyanation. The unconventional site selectivity is attributed to the in situ formation of 3-iodochromone and a formal 1,2-hydrogen atom transfer (HAT) process. Additionally, the synthesis of 2-cyanoquinolin-4-one has been achieved by employing the corresponding 2-aminophenyl enaminone as the substrate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Changfeng Wan, Yunyun Liu, Jie-Ping Wan
Summary: A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been developed via the reactions of enaminones, hydrazine hydrochloride, and internal alkynes using Rh catalysis. The cascade reactions demonstrate the remarkable high-order bond functionalization, involving the transformation of aryl C-H, ketone C=O, and alkenyl C-N bonds in the enaminones. This study highlights the individual advantage of enaminones in the design of novel and efficient synthetic methods.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiao Xiao, Puren Han, Jie-Ping Wan, Jianchao Liu
Summary: An efficient and general method for the synthesis of indolyl-C-glycosides has been developed. The method exhibits excellent stereoselectivity, a wide range of substrate applicability, and mild reaction conditions. It has also been successfully applied to large-scale reactions and diversified synthetic transformations.
Article
Chemistry, Multidisciplinary
Zukang Zhong, Lihua Liao, Yunyun Liu, Ming Zhang, Jie-Ping Wan
Summary: The annulation reactions of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans have been realized. Indoles were obtained via HNMe2-elimination-based aromatization with Zn(ii) catalysis, while 2-aminobenzofurans were produced via dehydrogenative aromatization with Fe(iii) catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Dingsheng Cao, Chaoli Wang, Jie-Ping Wan, Chengping Wen, Yunyun Liu
Summary: This paper describes the trifunctionalization of tertiary enaminones, specifically the selective gem- and vicinal diphosphorylation, enabling the synthesis of tunable alpha,alpha- and alpha,beta-diphosphoryl ketones. Additionally, the phosphorylation of the C-N bond with improved substrate tolerance has been achieved.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Demao Chen, Liyun Zhou, Yunyun Liu, Jie-Ping Wan
Summary: The direct three-component reactions of enaminones, aryl hydrazine hydrochlorides, and internal alkynes via Rh(iii) catalysis have enabled the synthesis of N-naphthyl pyrazoles. The use of simple substrates in these synthetic reactions results in the simultaneous construction of dual cyclic moieties, including a pyrazole ring and a phenyl ring, through the sequential formation of two C-N and three C-C bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Baoli Zhao, Xiaoting Yin, Haifeng Li, Kai Cheng, Jie-Ping Wan
Summary: A metal-free dioxygenative reaction of aryl diazonium salts with aryl alkynes for vicinal diketone synthesis has been developed. The major advantages of this synthetic method are aerobic oxygenation and organic dye-based photocatalysis. A photoredox mechanism involving free radical dioxygenation is proposed based on rational control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Jianchao Liu, Jie-Ping Wan, Yunyun Liu
Summary: This review highlights the recent progress in the development of electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens. It covers various reactions such as oxychalcogenation, carbochalcogenation, aminochalcogenation, halochalcogenation, and dichalcogenation. These studies are of great significance in the field of organic synthesis chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jingfeng Ye, Yunyun Liu, Jin Luo, Jie-Ping Wan
Summary: The synthesis of polyfunctionalized alkenes has been achieved through the transformation of enaminones, disulfides, and alcohols without the use of transition metals. Furthermore, the application of the alkene products in the synthesis of various sulfenyl heteroaryls has been demonstrated.
