Article
Chemistry, Organic
Leiqing Fu, Jie-Ping Wan
Summary: Enaminones play a significant role in organic synthesis as platform building blocks, allowing the formation of new chemical bonds through diverse cascade reactions. Transition metal catalysis has been a practical and powerful strategy in enaminone chemistry, leading to significant advances in the synthesis of structurally diversified organic products.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Qing Yu, Yunyun Liu, Jie-Ping Wan
Summary: The perfluoroalkylsulfonylation in enaminone C-H bonds has been achieved by using molecular iodine promotion and stable, inexpensive sodium perfluoroalkyl sulfinates as coupling partners, leading to the stereoselective synthesis of E-configurated alpha-perfluoroalkylsulfonyl enaminones.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Liangliang Song, Erik V. Van der Eycken
Summary: Multiple strategies have been developed for the synthesis of polycycles, relying on transition metal-catalyzed C-H activation followed by intermolecular annulation reactions. These methods offer rapid, concise, and efficient construction of diverse polycycles.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Sandeep Kumar, Akshay Kumar, Dharminder Sharma, Pralay Das
Summary: Directing groups are widely used for transition metal-catalyzed direct C-H bond functionalization, with recent advancements in utilizing free amine, hydroxyl and sulfhydryl as directing groups for the synthesis of heterocycles.
Article
Chemistry, Organic
Weiqiao Lan, Jiatong Zhu, Buweihailiqiemu Abulaiti, Genyuan Chen, Zhihao Zhang, Nan Yan, Jie-Ping Wan, Xiaomei Zhang, Lihua Liao
Summary: An efficient zinc-catalyzed amination reaction has been developed for the para-selective amination of free anilines and free phenols with quinoneimides, leading to C-N bond formation via a 1,6-addition pathway. This protocol not only offers a promising approach for constructing structurally diverse p-phenylenediamine compounds with excellent yields, but also extends the application of the quinoneimide-involved 1,6-addition reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Shanping Chen, Kai Hu, Wei Feng, Guojiang Mao, Yuxia Li, Guo-Jun Deng
Summary: A direct strategy for the synthesis of fused thienoindoles from substituted indoles and elemental sulfur has been reported. This method yields a range of structurally valuable fused thienoindoles in 51-78% yield under transition-metal-free conditions, potentially useful in pharmaceutical industry and organic functional materials.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Marc Font, Moises Gulias, Jose Luis Mascarenas
Summary: The selective functionalization of C(sp(3))-H bonds using transition-metal catalysis is an important transformation in modern synthetic chemistry, although it poses significant challenges. There has been notable progress in recent years, particularly in the development of new intermolecular reactions. Conversely, the research on assembling cyclic products from simple acyclic precursors using metal-catalyzed C(sp(3))-H bond activations has been relatively limited.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Prasanjit Ghosh, Deepan Chowdhury, Suman Dana, Mahiuddin Baidya
Summary: Transition-metal-catalyzed direct transformation of inert C-H bonds has significantly impacted mainstream organic synthesis, with free-amine functionality emerging as a potent directing group for the formation of C-C and C-heteroatom bonds.
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)
Review
Chemistry, Organic
Jyotshna Phukon, Arun Jyoti Borah, Sanjib Gogoi
Summary: Spirocyclic compounds play an important role in natural substances and have widespread applications in drug discovery and organic synthesis due to their structural rigidity and stereochemical recognition.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Supriya Rej, Naoto Chatani
Summary: Considerable advances have been made in the field of C-H functionalization, with special interest in C-H borylation due to its wide applications. Transition-metal-catalyzed regioselective strategies have been developed, but the use of precious metals and contamination by metal precursors limit their application in large-scale synthesis. Recent trends involve the use of transition-metal-free systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Liangliang Song, Gerardo M. Ojeda-Carralero, Divyaakshar Parmar, David A. Gonzalez-Martinez, Luc Van Meervelt, Johan Van Der Eycken, Jan Goeman, Daniel G. Rivera, Erik V. Van der Eycken
Summary: This report presents a ruthenium-catalyzed C-H activation/annulation process that can selectively modify the peptide backbone to produce functionalized isoquinolone scaffolds with high regioselectivity in a rapid and step-economical manner. The method allows for the production of fluorescent peptides, peptide conjugates with drugs, natural products, and other peptide fragments, providing a chemical approach for constructing novel peptide-pharmacophore conjugates.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Xinyu Chen, Na Yang, Wen Zeng, Lei Wang, Pinhua Li, Hongji Li
Summary: A mild dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates was reported, leading to the synthesis of dibenzo[b,e]azepine derivatives in moderate to good yields. Increasing steric hindrance at the C2-position of 1H-indoles directs the reaction towards a [2+2] cycloaddition pathway. Mechanistic investigations suggest that the reaction proceeds through a [2+2] cycloaddition followed by a ring expansion to form the [5+2] cycloaddition product.
CHEMICAL COMMUNICATIONS
(2021)
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.
Review
Chemistry, Organic
Arpana Tyagi, Naveen Yadav, Jabir Khan, Sanjay Singh, Chinmoy Kumar Hazra
Summary: Silicon-containing molecules have widespread applications in various research areas, and the transition-metal-free C-H silylation is an essential process for fabricating carbon-silicon bonds. This review focuses on recent developments in the field of silicon chemistry, particularly innovative transition-metal-free catalytic silylation using different strategies.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinbiao Ying, Ting Liu, Yunyun Liu, Jie-Ping Wan
Summary: A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been developed using enaminones and BrCF2CO2Et as starting materials with Na2CO3 as the catalyst. This method does not require any transition metal reagent and enables the annulative difluoromethylation by partial cleavage of the C=C double bond. Furthermore, treatment with hydrochloric acid in the same reaction system leads to the formation of beta-keto enoic acids via formal enaminone C-N carboxylation.
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.
