Article
Chemistry, Multidisciplinary
Velautham Saravanan, Masilamani Jeganmohan
Summary: This study describes a palladium-catalyzed tandem reaction of 7-oxabenzonorbornadienes with organic carboxylic acids, which produces cis-1,2-dihydro-l-naphthyl derivatives with moderate to good yields and high diastereoselectivity. A proposed reaction mechanism involving syn acylation, insertion, and diastereoselective ring-opening with 7-oxabenzonorbornadienes explains the reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Evgeniya S. Shutovskaya, Yulia P. Ustimenko, Alexey V. Tkachev, Julia V. Burykina, Alexander M. Agafontsev, Anastasiya V. Lastovka, Dmitriy N. Polovyanenko, Taisiya S. Sukhikh
Summary: In this study, the Pd-catalyzed cross-coupling reaction between α-pinene derivative - pinacarvone O-methyl oxime and aryl halides was described. Surprisingly, the formation of the C-C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The reaction conditions were carefully optimized and the reaction mechanism was proposed based on structural and computational data analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Erika Linde, Berit Olofsson
Summary: The diarylation and skeletal diversification of unstrained cyclic amines was explored to expand and modify their properties. A novel class of amino-substituted diaryliodonium salts was synthesized from cyclic amines and converted to highly functionalized diarylamines through a one-pot N-arylation/ring opening reaction. This strategy proved efficient in the late-stage functionalization of natural products and pharmaceuticals, and provided a wide variety of complex diarylamines. The method involves the introduction of two different aryl groups and the retention of an iodo-substituent, allowing for downfield diversification of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Lantao Liu, Fangyuan Cheng, Chenxiang Meng, An-An Zhang, Mingliang Zhang, Kai Xu, Naoki Ishida, Masahiro Murakami
Summary: A Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates. This method provides a convenient approach to chiral 2,3-dihydrobenzofurans with excellent enantioselectivities, and has been applied in the concise synthesis of analogues of cannabinoid receptor 2 agonists.
Article
Chemistry, Applied
Garazi Urgoitia, Maria Obieta, Maria Teresa Herrero, Luis Lezama, Raul Sanmartin
Summary: This paper discloses a palladium-catalyzed procedure for the transamidation of structurally diverse amides with amines using molecular oxygen as a palladium-activating agent. The reaction is carried out in a bio-degradable solvent and two different kinetically mechanisms are proposed based on several experimental results.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Junjie Meng, Hui He, Qianru Liu, Hanhong Xu, Huicai Huang, Shao-Fei Ni, Zhaodong Li
Summary: A PdII-catalyzed domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is described, which generates valuable functionalized compounds with excellent enantio- and diastereo-selectivity. The method allows the construction of multiple covalent bonds and stereocenters in an efficient and atom-economical manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Shuntao Huang, Teng Liu, Jingpeng Li, Qi Yang, Shuyan Zhan, Chao Huang
Summary: An interesting ring-closing/ring-opening cascade reaction selectively induced by aliphatic primary amine for the synthesis of functionalized aminomaleimides is described. This work features phenolic hydroxyl as a traceless directing group that forms a critical six-membered intermediate and then undergoes lactone ammonolysis/intramolecular amidation sequence. This two-step, one-pot practical protocol has broad substrate scope (39 examples) and delivers structurally diverse aminomaleimides in good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Applied
Jiupeng Liu, Jiaqi Li, Bowen Ren, Yun Zhang, Linyi Xue, Yanying Wang, Jingjing Zhao, Puyu Zhang, Xuejun Xu, Pan Li
Summary: The reactivity of N-tosyl vinylaziridines towards arynes has been demonstrated in mild and transition-metal-free conditions, leading to the formation of 2-(phenanthren-9-yl)ethan-1-sulfamides in moderate to good yields. Selective synthesis of N-H and N-aryl products was achieved using different conditions, involving a cascade process of sequential Diels-Alder reaction, ring-opening aromatization, ene-reaction, and selective N-arylation reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jun-An Xiao, Huan Zhang, Xue-Ling Luo, Ru-Fang Meng, Wei Wang, Wei-dong Lu, Wei Su, Chenxiang Lin, Peng-Ju Xia, Hua Yang
Summary: A palladium-catalyzed ring-opening [3 + 2]-annulation reaction was developed for the synthesis of seven-membered benzosultams from spirovinylcyclopropanyloxindoles and cyclic N-sulfonylimines. The reaction yielded a wide range of compounds with both a quaternary center and axially chiral biaryl scaffolds, with an average yield of 87% and moderate to excellent diastereoselectivities. Enantioenriched benzosultams were also successfully synthesized in good yields with excellent atropoenantioselectivities using the Pd-2(dba)(3)/(S,S,S)-SKP ligand. The practical utility of this method was demonstrated through gram-scale reactions and diversified synthetic transformations.
Article
Chemistry, Multidisciplinary
Aparna Tyagi, Naveen Yadav, Jabir Khan, Sankalan Mondal, Chinmoy Kumar Hazra
Summary: A mild, efficient, and metal-free synthetic protocol for the synthesis of beta-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol% catalyst loading and affords beta-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON = 842. Further, the Hammett correlation study was also performed to identify the rate-determining step.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Xiao-Fei Fu, Qiang Zhao, Wen-Xian Zhao
Summary: A copper-catalyzed three-component tandem reaction involving alkenes, sulfonyl azides, and alcohols has been described for the synthesis of valuable beta-alkoxy amines. This method is practical and cost-effective, showing good yields and tolerance towards various functional groups.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yiding Wang, Lei Shen, Helin Wang, Yixin Luo, Qingle Zeng
Summary: The ring-opening addition reaction of activated vinyl cyclopropanes with N-tosylhydrazones in the presence of palladium(0) and triphenylphosphine yields N-tosylhydrazone butenylmalonate compounds. Aromatic aldehyde-derived N-tosylhydrazones produce both terminal and internal N-allylated products, with the terminal products being the major ones. On the other hand, ketone-derived tosylhydrazones only yield terminal addition products. The transformation relationship between the terminal and internal N-allylated products is also observed. A reasonable mechanism based on preliminary experimental results is proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Youhei Takeda, Kazuya Toyoda, W. M. C. Sameera, Norimitsu Tohnai, Satoshi Minakata
Summary: A novel palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki-Miyaura arylative cross-coupling has been developed to synthesize enantioenriched 3,3-diarylpropylamines. The mechanism of the reaction was rationalized using density functional theory, with transition states of the selectivity-determining ring-opening step systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Wen-Jing Yan, Hai-Yong Tu, Zhiyong Liao, Xiao-Qin Shen, Xing-Guo Zhang
Summary: A method for constructing the indane skeleton was described, involving a palladium-catalyzed ring-opening diarylation of Cyclobutanols with aryl 1,2-dihalides. The reaction proceeds through beta-carbon elimination and subsequent alpha-carbon arylation of ketone, resulting in the formation of 2-acylindanes in yields of 42-93%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
An-Qi Miao, Meng Zhou, Jing-Long Chen, Shi-Chao Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: An asymmetric addition of arylboronic acids to pyrazolinone ketimines was reported using a palladium/chiral N,N'-disulfonyl bisimidazoline (Bim) catalytic system, yielding enantioenriched 4-amino-5-pyrazolones with high yields and high enantiomeric excess. The reaction demonstrated excellent compatibility between pyrazolinone ketimines and arylboronic acids, providing an enantioselective access to chiral aza-heterocycles bearing alpha-tertiary amines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zhiping Yang, Qingwei Du, Yanxin Jiang, Jun (Joelle) Wang
Summary: In this study, a highly efficient, versatile, and universal method for synthesizing gamma-amino acid and gamma-amino phosphonic acid derivatives was developed. The method allows for good yields of chiral products with high levels of enantiocontrol and regioselectivity.
Article
Chemistry, Organic
Mingliang Li, Jun (Joelle) Wang
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Xiaodong Gu, Qingwei Du, Weijian Song, Jun (Joelle) Wang
Summary: An efficient and practical method for synthesizing heterocyclic nucleosides is developed, employing a catalyst-free [3+2] annulation reaction between alpha-purine-substituted acrylates and nitrones. The reaction exhibits excellent tolerance towards functional groups and is conducted under mild conditions, using the green and sustainable solvent 2-methyltetrahydrofuran (2-MeTHF). Unlike other reactions with electron-deficient olefin dipolarophiles, different regioselective cycloaddition products were observed in this study. The resulting isoxazolidinyl nucleosides demonstrate good to excellent yields and hold promising applications in biochemistry and medicinal chemistry.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Baohua Cai, Yuan Cui, Jian Zhou, Yong-Bin Wang, Limin Yang, Bin Tan, Jun (Joelle) Wang
Summary: A Cu/CPA co-catalytic system was developed to achieve direct hydrophosphinylation of alkynes with phosphine oxides, delivering novel axially chiral phosphorus-containing alkenes with high yields and excellent enantioselectivities (up to 99% yield and 99% ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jian Zhou, Ling Meng, Shujuan Lin, Baohua Cai, Jun (Joelle) Wang
Summary: We report a straightforward Pd-catalyzed ring-opening hydrophosphinylation reaction of methylenecyclopropanes (MCPs) via highly selective C-C bond cleavage. This method allows for rapid and efficient access to a wide range of chiral allylic phosphine oxides in good yields and high enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Xing Sheng, Jiayi Xian, Shuting Liu, Xiangyu Zhang, Bin Li, Jun Wang, Xiuwen Chen, Feng Xie
Summary: This study describes a green palladium-catalyzed nitroarene/nitrile reductive cross-annulation chemistry for the straightforward synthesis of pyrrolo[1,2-a]quinoxaline derivatives. Nitriles are activated as carbon synthons to form intramolecular C-N and C-C bonds. The synthetic protocol offers broad substrate scope, excellent functional group tolerance, and uses water and inexpensive HCOONa/HCOOH as the solvent and hydrogen donors, respectively. The catalyst can be conveniently recycled and reused multiple times without significant deactivation. This study provides an important platform for converting bulk chemical motifs into value-added functional frameworks.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Yanxin Jiang, Kwai Wun Cheng, Haoyang Zhang, Zhiping Yang, Jun Wang
Summary: A new palladium-catalyzed asymmetric Suzuki-Miyaura coupling is demonstrated using a unique monophosphine ligand, Azaphos. This method offers a novel ligand framework for the synthesis of axially chiral compounds via asymmetric Suzuki-Miyaura coupling reactions.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Sifeng Li, Lijing Fang, Qian Dou, Taimin Wang, Bin Cheng
Summary: Organophosphorus compounds are widely used in various disciplines, and their preparation has received considerable attention. While numerous review articles have been published on the preparation of organophosphorus derivatives, the construction of P-X (X = C) bonds has not been thoroughly summarized. This overview focuses on the oxidative cross-coupling of P-H compounds with hetero-nucleophiles (X-H) containing N, O, S, or Se atoms. The synthetic methods are categorized into six types based on the route to obtain the P-X compounds. Various compounds, including amines, arylhydrazines, amides, and more, can serve as suitable coupling partners for the construction of P-X bonds through distinct oxidative cross-coupling pathways.
Article
Chemistry, Multidisciplinary
Qingjing Yang, Jian Zhou, Jun (Joelle) Wang
Summary: An enantioselective hydrophosphination reaction of alkenyl isoquinolines is achieved using a copper-chiral diphosphine ligand catalyst. This method provides a straightforward and efficient synthesis of chiral phosphines containing an isoquinoline moiety, with high yields and excellent enantioselectivities. Additionally, these chiral phosphine products can serve as useful bidentate P,N-ligands with potential applications in asymmetric catalysis.
Article
Chemistry, Organic
Jiexiong Mai, Ziwei Huang, Shaohuan Lv, Quan Chen, Rongrong Chen, Feng Xie, Jun Wang, Bin Li
Summary: An efficient and visible light-promoted cascade N-alkylation/amidation reaction between quinazolin-4(3H)-ones and benzyl halides/allyl halides has been reported for the first time, providing a convenient approach for synthesizing quinazoline-2,4(1H, 3H)-diones. This cascade reaction shows good functional group tolerance and can also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments reveal the crucial role of K2CO3 in this transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yixiao Zhang, Pengwei Xu, Qiongli Zhao, Jun Wang, Zhongxing Huang
Summary: Substituted malonic esters are valuable substrates for desymmetrization to tertiary and quaternary stereocenters. A new variation of the desymmetrization has been developed for monosubstituted malonic esters using a pipecolinol-derived tetradentate ligand. This method allows for the preparation of structurally diverse tertiary stereocenters with good yields and enantioselectivity. The enantioenriched products have been demonstrated to have synthetic utility in a mild amination procedure to synthesize chiral amino alcohols.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Xiao Zhang, Qian Zhou, Yue Zhou, Zihao Wang, Jun Wang, Mingfu Wang
Summary: A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective hydroallylation reaction has been developed for the synthesis of chiral chromanes and thiochromanes with high enantioselectivities. These compounds can serve as important intermediates for the synthesis of bioactive compounds containing oxygen and sulfur atoms. Moreover, the synthesized chromanes and thiochromanes exhibit antioxidant and anti-inflammatory effects, making them potential lead compounds for the development of drugs in those areas.
Review
Chemistry, Organic
Dou Qian, Wang Taimin, Li Sifeng, Fang Lijing, Zhai Hongbin, Cheng Bin
Summary: The article introduces the importance of carbon dioxide as a greenhouse gas and the methods of synthesizing carboxylic acids using CO2 in organic chemistry. It also discusses the application of transition metal catalysis and photocatalytic synthesis technology in the conversion and utilization of CO2.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Yiliang Zhang, Yanxin Jiang, Mingliang Li, Zhongxing Huang, Jun (Joelle) Wang
Summary: In this study, a new method for the synthesis of chiral cyclopropanes with high stereoselectivity was reported, which has important potential applications.
Article
Chemistry, Multidisciplinary
Xiaodong Gu, Kexin Liu, Limin Yang, Chengyi Xie, Mingliang Li, Jun (Joelle) Wang
Summary: This study reports a nickel-catalyzed asymmetric alpha-heteroarylation of ketones with fluorinated heteroarenes, providing products with all-carbon quaternary stereocenters in good yields and high enantiomeric excess values. The reaction conditions were also shown to be compatible with late-stage diversification of drug molecule donepezil.
