Article
Biochemistry & Molecular Biology
Vilija Kederiene, Indre Jaglinskaite, Paulina Voznikaite, Jolanta Rousseau, Patrick Rollin, Algirdas Sackus, Arnaud Tatibouet
Summary: The Cu-catalyzed N-arylation method described in this study is an efficient tool for chemical modification of aromatic heterocycles, offering a relatively cheap and experimentally simple way to afford N-substituted products in moderate to high yields. The structures of the new heterocyclic compounds were confirmed by NMR spectroscopy and HRMS investigation.
Article
Chemistry, Multidisciplinary
Saidkhodzha Nematulloev, Arunachalam Sagadevan, Badriah Alamer, Aleksander Shkurenko, Renwu Huang, Jun Yin, Chunwei Dong, Peng Yuan, Khursand E. Yorov, Azimet A. Karluk, Wasim J. Mir, Bashir E. Hasanov, Mohamed Nejib Hedhili, Naveen M. Halappa, Mohamed Eddaoudi, Omar F. Mohammed, Magnus Rueping, Osman M. Bakr
Summary: This study reports the synthesis of atomically precise copper hydride nanoclusters with a controlled defect, which were demonstrated to be highly selective catalysts for C-C cross-couplings. The work highlights the potential of defective nanoclusters as model systems for investigating individual defects, correlating defects with physicochemical properties, and rationally designing new nanoparticle catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Christian Frabitore, Jerome Lepeule, Tom Livinghouse
Summary: Nitrogen-containing heterocycles are the main components of most FDA-approved small-molecule pharmaceuticals. This article describes a synthetic method to produce saturated N-heterocyclic drug scaffolds with an internal alkyne. By treating compounds and conducting reactions, products such as piperidines and pyrrolidines can be obtained.
Article
Multidisciplinary Sciences
Xiao Hai, Yang Zheng, Qi Yu, Na Guo, Shibo Xi, Xiaoxu Zhao, Sharon Mitchell, Xiaohua Luo, Victor Tulus, Mu Wang, Xiaoyu Sheng, Longbin Ren, Xiangdong Long, Jing Li, Peng He, Huihui Lin, Yige Cui, Xinnan Peng, Jiwei Shi, Jie Wu, Chun Zhang, Ruqiang Zou, Gonzalo Guillen-Gosalbez, Javier Perez-Ramirez, Ming Joo Koh, Ye Zhu, Jun Li, Jiong Lu
Summary: Heterogeneous geminal-atom catalysts (GACs) offer a new avenue for the sustainable manufacture of fine chemicals by pairing single-atom sites in specific coordination and spatial proximity.
Article
Chemistry, Multidisciplinary
Johanne Ling, Antoine Bruneau-Voisine, Guillaume Journot, Gwilherm Evano
Summary: In this study, a general copper-catalyzed carbonylative cross-coupling between amines and alkyl iodides was reported. The reaction showed good efficiency and broad substrate scope, making it potentially valuable for industrial applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Xinmiao Huang, Ling Tang, Zhiyong Song, Shuangshuang Jiang, Xianmao Liu, Ming Ma, Bo Chen, Yuanhong Ma
Summary: A nickel catalysis system has been developed for the desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with aryl bromides to form diverse biaryl compounds. The isolated and confirmed Ar-Ni(II)-SO(2)CF3 complex with a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species provides solid evidence for understanding the C(Ar)-SO2 bond activation and reaction mechanism.
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
Ren-Guan Miao, Weiqi Dai, Xinxin Qi, Xiao-Feng Wu
Summary: C-S bond formation is important in organic synthesis, material science, and medicinal chemistry. This study presents a nickel-catalyzed desulfonative cross-coupling reaction for the synthesis of unsymmetrical thioethers. Using readily available sulfonyl chlorides as both electrophiles and sulfur precursors, various asymmetric thioethers can be synthesized with good yields and functional group tolerance.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Organic
Dmitry A. A. Dulov, Tatiana V. V. Magdesieva
Summary: It has been demonstrated that inexpensive and readily available N,N'-diaryldihydrophenazines can effectively replace Ir(III)- and Ru(II)-based photocatalysts in the dual photoredox/Ni(II)C-N coupling of aryl halides with a wide range of anilines, as shown by 32 examples. This efficient and operationally simple approach to diarylamines can be scaled up using a flow apparatus.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Peng Wu, Jas S. Ward, Kari Rissanen, Carsten Bolm
Summary: Copper-catalyzed cross-coupling reactions of alpha-bromoaryl NH-sulfoximines with elemental sulfur were used to synthesize benzo[d][1,3,2]dithiazole-1-oxides, which belong to a new class of three-dimensional heterocycles. The reactions exhibited good functional group and heterocycle tolerance under mild conditions. Moreover, the initial cross-coupling products could be converted to unprecedented cyclic sulfonimidamides derivatives through imination/oxidation. Additionally, a seven-membered heterocycle was obtained by a ruthenium-catalyzed ring-expansion with ethyl propiolate.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Qi Yukki Li, Samuel N. Gockel, Grace A. Lutovsky, Kimberly S. DeGlopper, Neil J. Baldwin, Mark W. Bundesmann, Joseph W. Tucker, Scott W. Bagley, Tehshik P. Yoon
Summary: Reactions that allow for the formation of carbon-nitrogen, carbon-oxygen, and carbon-carbon bonds are crucial in synthetic chemistry. This study presents a copper-mediated, net-oxidative decarboxylative coupling reaction under visible-light irradiation, which enables the conversion of substrates without requiring harsh reaction conditions.
Article
Chemistry, Organic
Ge Liang, Jing-Hao Wang, Tao Lei, Yuan-Yuan Cheng, Chao Zhou, Ya-Jing Chen, Chen Ye, Bin Chen, Chen-Ho Tung, Li-Zhu Wu
Summary: This study presents an aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols, showing high functional group tolerance and selectivity. Mechanistic studies reveal the crucial role of disulfide radical cation in the visible-light catalysis of aerobic thiolation, allowing selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction by controlling the equivalent ratio of substrates.
Article
Chemistry, Multidisciplinary
Santosh Kumar Sahu, Prabhupada Choudhury, Pradyota Kumar Behera, Tanmayee Bisoyi, Rashmi Ranjan Sahu, Abinash Bisoyi, Koteswara Rao Gorantla, Bhabani S. Mallik, Manoj Mohapatra, Laxmidhar Rout
Summary: The study presents a new protocol for Sonogashira cross-coupling reaction using the cheap and commercially available CuSeO3·2H2O catalyst, resulting in high yields of products under mild conditions without the need for ligands. This marks the first use of an oxygen-bridged copper-based bimetallic catalyst for C-sp-C-sp2 Sonogashira cross-coupling reactions under mild conditions, demonstrating a palladium-free reaction up to a limit of 0.2 ppm.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Andrew C. Jones, William I. Nicholson, Jamie A. Leitch, Duncan L. Browne
Summary: The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is efficient and green, achieving reductive C-C bond formation under a mechanochemical manifold. The mechanical action provided by ball milling allows for the use of a variety of zinc sources to turnover the nickel catalytic cycle, resulting in the synthesis of 28 cross-electrophile coupled products.
Article
Chemistry, Physical
Huan Zhou, Zhong-Liang Li, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: Transition-metal-catalyzed asymmetric C-(sp(3))-C cross-coupling is an efficient method for the rapid synthesis of enantioenriched molecules. Chiral copper catalysts have been designed to promote a variety of asymmetric radical C(sp(3))-C cross-coupling reactions with high efficiency and enantioselectivity. The key to success lies in the design of chiral ligands to initiate the reaction and achieve enantiocontrol over the highly reactive prochiral alkyl radical species.
Review
Chemistry, Organic
Xiao Yun Chen, Xiaotong Zhang, Jie-Ping Wan
Summary: Enaminones and analogous stable enamines are widely used as platform building blocks in organic synthesis for constructing heterocyclic compounds, especially N-heterocycles. Recently, synthetic protocols based on the C-N bond cleavage of enamines have achieved notable success in the development of transition metal-free heterocyclic product synthesis.
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.