Article
Chemistry, Multidisciplinary
Xuefeng Tan, Xiaoyan Hou, Torben Rogge, Lutz Ackermann
Summary: This study achieved the electrochemical three-component assembly of isoquinolines using ruthenium electro-catalyzed C-H/N-H functionalization, demonstrating a robust electrocatalysis with ample substrate scope, efficient electrooxidation, and an operationally friendly procedure. Furthermore, detailed mechanistic studies and unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle supported an unusual ruthenium(II/III/I) regime.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Vavilapalli Suresh, Muniganti Naveen Kumar, Attunuri Nagireddy, Maddi Sridhar Reddy
Summary: The Rh-catalyzed C-H activation of arenes for oxidative annulations with alkynes is an efficient method to form polycyclic scaffolds. In this study, a regioselective triple annulation of enaminones with hydroxyl-alkynoates via double C-H functionalization was achieved by rhodium catalysis, resulting in polycyclic naphtho-pyran scaffolds. The regioselectivity was controlled by the secondary coordination of hydroxyl group in alkynoate.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Meng-Yang Chang, Chun-Yi Lin
Summary: In this study, a one-pot construction method for diversified sulfonyl flavones was developed. The alpha-sulfonyl o-hydroxyacetophenones were reacted with substituted nitriles through a K2CO3-mediated (5+1) stepwise annulation under open-flask atmosphere conditions. This method offers intermolecular and intramolecular ring-closure pathways by forming a carbon-oxygen single bond, a carbon-carbon double bond, and cleaving a carbon-nitrile triple bond.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Lin Li, Xin-Lian Liu, Jin-Yan Liang, Yong-Yu He, Ai-Jun Ma, Wei-Feng Wang, Jin-Bao Peng
Summary: A palladium-catalyzed dicarbonylation reaction of alpha-iodo-substituted ACPs has been developed for the synthesis of carbamoyl-substituted indenones. Two carbonyl groups are incorporated into the product by cleaving the proximal C-C bond of the ACPs. A broad range of carbamoyl-substituted indenones are efficiently prepared with good to excellent yields.
Article
Chemistry, Organic
Gang Yang, Lin Yao, Guojiang Mao, Guo-Jun Deng, Fuhong Xiao
Summary: We have reported a metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines via [4 + 2] cycloaddition reaction using readily available 2-aminobenzaldehydes and ketones as starting materials. Different quinoline derivatives can be selectively synthesized by changing the type of ketones. O-2 and dimethyl sulfoxide (DMSO) as co-oxidants play an important role in the synthesis of indenoquinolinones. This condensation/oxidation strategy involves the formation of C-N, C-C, and C-O bonds, with the advantages of high yields and a broad substrate range.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Gang Yang, Lin Yao, Guojiang Mao, Guo-Jun Deng, Fuhong Xiao
Summary: A metal-free protocol for the synthesis of indenoquinolinones and 2-substituted quinolines using readily available 2-aminobenzaldehydes and ketones has been reported. Different quinoline derivatives can be selectively synthesized by altering the type of ketones.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yi Luo, Wei-Yi Pu, Yan-Jun Xu, Lin Dong
Summary: Rh(III)-catalyzed efficient cascade annulation has been used to selectively construct various spiro-[imidazole-indene] derivatives using versatile propargyl alcohols. The type of propargyl alcohol plays a crucial role in tuning the combination state and controlling the formation of different products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yijiao Feng, Jing He, Yueting Wei, Jianwei Xie, Ping Liu
Summary: Cascade reactions of 1,3-diarylpropane-1,3-dione or unsaturated ketones with arylsulfonyl hydrazide have been achieved via the presence of an iodine source, leading to the synthesis of fully substituted C4-sulfenylated pyrazoles. This method is efficient and practical, utilizing readily available starting materials and providing a useful strategy for constructing different arylthio-substituted pyrazole skeletons.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wei-Jung Chiu, Ting-Yen Chu, Indrajeet J. J. Barve, Chung-Ming Sun
Summary: A Pd(II)-catalyzed [5 + 2] annulation reaction between N-triflyl aryl indoles and α,γ-substituted allenoates for the synthesis of indole-fused benzodiazepines is described. The use of N-acetylated valine amino acid as a ligand and DMSO as a cosolvent enhances the efficiency of this protocol. The reaction mechanism involves C-H activation, cyclopalladation, coordination, migratory insertion, reductive elimination, and [1,3]-H shift.
Article
Chemistry, Organic
Peng-Wei Zhu, Hong-Mei Ma, Yang Li, Ling-Zhen Miao, Jie Zhu
Summary: An electro-triggered cascade cyclization strategy is presented for the synthesis of phosphinyl-substituted N-heterocycles. This environmentally friendly method does not require external metal catalyst, oxidant, or heating. Mechanistic studies show that anodic oxidation of H-phosphorus compounds generates the key P centered radical, while cathodic reduction simultaneously releases molecular hydrogen or methane. This protocol offers simple operation, broad substrate scope, clean and mild conditions, and atom and step economy for the formation of heterocycle-containing organophosphorus scaffolds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Shurui Zhang, Shulei Hu, Kean Wang, Zhao Yang, Hong Liu, Jiang Wang
Summary: This paper describes the transition-metal-catalyzed C-H activation and annulation reactions of pyrazolidinones with 4-vinyl-1,3-dioxolan-2-one or vinylene carbonate. This protocol provides two types of pyrazolo[1,2-a]cinnolines, which are essential assets for the development of bioactive compounds. The practicality of the synthesis is demonstrated with 44 examples, and a possible mechanism for these reactions is proposed based on preliminary studies and previous reports, with no oxidant added to both reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Qinghe Gao, Zhenhua Sun, Qinfei Xia, Ruonan Li, Wenlong Wang, Siwei Ma, Yixin Chai, Manman Wu, Wei Hu, Peter Abranyi-Balogh, Gyorgy M. Keseru, Xinya Han
Summary: A new general synthesis method has been developed to prepare pharmaceutically important azolo[1,5-a]pyrimidines starting from commonly available 3(5)-aminoazoles, aldehydes, and triethylamine. This direct and practical strategy allows the construction of a variety of compounds, including pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines, with the capability to synthesize zaleplon, a clinically used drug.
Article
Chemistry, Organic
Wen-Zhe Wang, Hao-Ran Shen, Jian Liao, Wei Wen, Qi-Xiang Guo
Summary: This work reports a catalytic asymmetric tandem reaction involving a chiral aldehyde catalyzed conjugated addition and an intramolecular lactamization. Fully substituted pyroglutamic acids bearing three vicinal chiral centers were successfully generated in good-to-excellent yields and stereoselectivities under the optimal reaction conditions. A reasonable reaction mechanism is proposed to explain the observed stereoselective control results.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Min Liu, Kelu Yan, Jiangwei Wen, Weihua Liu, Mingyu Wang, Lina Wang, Xiu Wang
Summary: A method using rhodium(III) catalysis for the synthesis of substituted 1-hydroxy-2-naphthaldehydes through the reaction of enaminones with vinylene carbonate has been proposed, providing an alternative approach for the synthesis of these compounds with yields ranging from 49-84%. Preliminary mechanistic studies and hydroxyl-directed derivatization reactions of 1-hydroxy-2-naphthaldehydes were also conducted.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Qiang Ma, Ming Li, Zhuo Chen, Shao-Fei Ni, James S. Wright, Li-Rong Wen, Lin-Bao Zhang
Summary: An electrochemical protocol was developed for the synthesis of 2,3-disubstituted quinolines. The method is simple, mild, and does not require noble catalysts or external oxidants. It shows excellent regioselectivity and can tolerate various functional groups. The scaled-up experiment and follow-up procedures demonstrated the practicality of electrochemical synthesis.
Article
Chemistry, Organic
Liu-Liang Mao, An-Xi Zhou, Xian-Hong Zhu, Li-Xia Quan, Fayun Chen, Jie-Ping Wan, Yin-Long Lai
Summary: In this study, a visible-light-mediated tandem phosphorylation/cyclization reaction of N-arylacrylamides with H-phosphine oxides has been developed for the synthesis of phosphorylated oxindoles. This efficient and facile method allows for the construction of a C-P bond and triggers the formation of a C-C bond with good compatibility with functional groups under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(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.
