Article
Chemistry, Organic
Hongxiang Li, Wangyu Shi, Chang Wang, Hao Liu, Wei Wang, Yongjun Wu, Hongchao Guo
Summary: A successful phosphine-catalyzed cascade annulation of Morita-Baylis-Hillman (MBH) carbonates and diazenes was achieved, giving tetrahydropyrazole-fused heterocycles bearing two five-membered rings in moderate to excellent yields. The reaction exhibited an unprecedented reaction mode of MBH carbonates, where two molecules of MBH carbonates were fully incorporated into the ring system.
Article
Chemistry, Multidisciplinary
Juan Ye, Yilu Luo, Gailing Huang, Yang Wang
Summary: The detailed mechanism and role of the catalyst in the PPh3-catalyzed [3+6] annulation reaction of MBH carbonate and dicyanoheptafulvene were systematically investigated using a DFT method. The C-O bond cleavage was found to be the rate-determining step, while the reaction between allylic phosphorus ylide and dicyanoheptafulvene determined the regioselectivity with α-addition occurring prior to γ-addition. PPh3 promoted the release of BocO(-) anions primarily by alleviating the electron density between the Cγ-O1 bonds.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Siti Nur Fairuz Binte Sheikh Ismail, Binmiao Yang, Yu Zhao
Summary: In this study, a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones was successfully achieved, leading to the construction of a novel spirocyclic tetrahydroquinoline scaffold with high stereoselectivity.
Article
Chemistry, Organic
Tamilarasu Murugesan, Afna Elikkottil, Alagiri Kaliyamoorthy
Summary: Herein, we report a palladium-catalyzed regioselective C3-allylic alkylation of 2-aryl imidazopyridines with MBH carbonates. This strategy allows for the synthesis of diverse C3-allylated imidazopyridines, and their structures have been confirmed by X-ray analysis. Furthermore, the reaction can be easily scaled up and the resulting product can be manipulated into synthetically useful entities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yue Ren, Wangyu Shi, Yi Tang, Shixiang Piao, Songcheng Yu, Yongjun Wu, Hongchao Guo
Summary: A series of gamma-substituted MBH carbonates were synthesized and reacted with electrophilic exocyclic alkenes through phosphine-catalyzed annulations, resulting in the formation of valuable spirocyclopentenes with moderate to excellent yields and diastereoselectivities. The annulation process tolerates a wide range of MBH carbonates with gamma-hydrogen, alkenyl, and alkynyl substituents. Notably, this annulation involves the beta, gamma, and delta carbons of MBH carbonates, which is unprecedented.
Article
Chemistry, Organic
Xing Guo, Boming Shen, Chang Liu, Hongyue Zhao, Xuechen Li, Peiyuan Yu, Pengfei Li
Summary: Based on the frontier molecular orbital theory, two types of modified enones have been designed and successfully applied in the chiral phosphine-catalyzed stereoselective [1 + 4]-annulation of MBH carbonates. The reaction proceeds smoothly under mild conditions, exhibiting excellent functional group tolerance and providing a broad scope of enantioenriched 2,3-dihydrofurans with high efficiency. DFT calculations have been used to guide the design of additional enones and understand the origin of stereoselectivity. Furthermore, this method explores the application scope of enones and enriches the chemistry of [1 + 4]-annulations of MBH carbonates for the preparation of optically active multifunctional 2,3-dihydrofurans.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Huamin Wang, Yibo Wei, Yuqiang Li, Shuangshuang Long, Li-Juan Sun, Shixiong Li, Ying-Wu Lin
Summary: A new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was developed using [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This process allows for the efficient construction of stereogenic carbon centers and remote C-Ar-N atropisomeric chirality. The method exhibits mild reaction conditions, high efficiency, scalability, and a broad substrate scope.
Article
Chemistry, Organic
Zhen-Hui Yan, Run Lu, Cheng Peng, Jie Tang, Huaying Fang, Gu Zhan, Xiang-Hong He, Wei Huang
Summary: A series of polyfunctionalized spiro-oxindole dihydropyridine frameworks have been synthesized via an efficient Sc3+-catalyzed one-pot stepwise reaction. This transformation involves the cleavage and formation of multiple C-X/C-C bonds, enabled by N-olefination, Meinwald rearrangement, and inverse-electron-demand aza-Diels-Alder reaction. The advantages of this approach include readily available starting materials, mild reaction conditions, and high chemoselectivities and yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yingying Ren, Qishun Yu, Chengrong Lu, Bei Zhao
Summary: The catalytic enantioselective Michael addition of α,β-unsaturated ketones with malononitrile was successfully achieved using rare-earth metal amides and chiral phenoxy-functionalized TsDPEN ligands. The optimal reaction conditions provided the desired products in excellent yields and good to high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Marta Papis, Raffaella Bucci, Alessandro Contini, Maria Luisa Gelmi, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Camilla Loro
Summary: A phosphine-catalyzed domino assembly of six units of 2-bromomethyl acrylates was developed to synthesize polyalkenyl adducts containing two cyclohexenyl rings. This method involves initial dimerization and subsequent trimerization of the substrate, resulting in the formation of seven carbon-carbon bonds and four stereocenters. The protocol has also been successfully scaled up to gram-scale experiments.
Article
Chemistry, Multidisciplinary
Akshitha Selvaraj, Marie Cordier, Marc Devillard, Gilles Alcaraz
Summary: A methodological approach for the preparation of unconventional DTE-based photochromic phosphines is reported in this study, and the influence of different linkers on the photochromism and phosphinyl group basicity is studied and evaluated.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Ayumi Inami, Yuji Nishii, Koji Hirano, Masahiro Miura
Summary: In this study, a new synthetic method was developed using vinyl selenone as a surrogate for phenylacetylene in the Rh-catalyzed annulative coupling reaction. This method successfully produced 3,4-nonsubstituted isoquinoline compounds. The reaction conditions were mild and the vinyl selenone could be recovered and recycled.
Article
Chemistry, Organic
Yang An, Xiao-Yan Zhang, Ya-Nan Ding, Yuke Li, Xue-Yuan Liu, Yong-Min Liang
Summary: This study synthesized ferrocenes with planar chirality using palladium/chiral norbornene cooperative catalysis and axial-to-planar diastereoinduction. The chiral norbornene was used to control the aromatic axial chirality and induce the planar chirality of ferrocene through C(sp2)-H activation.
Article
Chemistry, Applied
Zhenhui Xu, Wangqin Zhang, Chao Xu, Tao Liu, Zhensheng Zhang, Changdi Zheng, Dingguo Song, Weihui Zhong, Fei Ling
Summary: In this study, a cobaltaelectro-catalyzed dehydrogenative [4+2] annulation of arylphosphinamides with alkynes was proposed, which selectively constructs a range of cyclic phosphinamide derivatives. Picolinic acid acts as a ligand to promote this transformation. A total of 38 examples demonstrate broad substrate scope, sufficient functional tolerance, and excellent regioselectivity. No additional oxidants or electrolytes are required, and gram-scale synthesis, late-stage diversification, and removal of the directing group can be achieved. Cyclic voltammetry and kinetic isotope experiments provide a better understanding of the reaction mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Hanyuan Li, Zhengjie He
Summary: This study reports a chiral phosphine-catalyzed asymmetric annulation reaction, which efficiently synthesizes enantio-enriched polysubstituted cyclopentenes with high stereoselectivity.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Yu Fu, Jian Huang, Yuzhou Wu, Xiaohong Liu, Fangrui Zhong, Jiangyun Wang
Summary: This study successfully achieved the photobiocatalytic cross-coupling of aryl halides using a designer artificial dehalogenase, demonstrating high synthetic value. The research results suggest the optimization of dual catalysis through a genetically encoded chromophore and site-specific modified cofactor, potentially expanding the catalytic repertoire of artificial photoenzymes for various organic transformations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Xunbo Lu, Yulong Bai, Jingyang Qin, Nan Wang, Yuzhou Wu, Fangrui Zhong
Summary: The implementation of a distinct mechanical activation strategy in catalysis has enhanced catalytic stability and performance, allowing for solvent-free C-H amination reactions. This approach can save precious catalysts and enrich the techniques of mechanosynthesis.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Dangui Wang, Wentao Zhang, Xunbo Lu, Hongwei Zhou, Fangrui Zhong
Summary: Novel cinchona alkaloid derived iodide catalysts were developed for the enantioselective oxidative alpha-amination of 2-oxindoles, providing various functionalized spiropyrrolidine oxindoles in high yields and with good enantioselectivities. This iodide/ROOH catalytic system features a one-step synthesis of a catalyst with multiple functionalities, ease of operation, and good scalability, thereby enriching the repertoire of iodide catalysis for enantioselective oxidative coupling reactions.
Article
Chemistry, Multidisciplinary
Jingyang Qin, Tong Zhou, Tai-Ping Zhou, Langyu Tang, Honghua Zuo, Huaibin Yu, Guojiao Wu, Yuzhou Wu, Rong-Zhen Liao, Fangrui Zhong
Summary: Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles with excellent optical purity. This method is valuable in enlarging the toolbox for atropochiral amine derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Yaming Deng, Quan Zhou, Yuzhou Wu, Xi Chen, Fangrui Zhong
Summary: Natural products, highly complicated organic molecules, are important resources in medicine. FMOs, a type of enzyme, catalyze oxidation reactions with selectivity and are involved in the synthesis of natural products. Understanding the mechanisms and applications of FMOs expands our knowledge of these powerful enzymes and provides effective tools for biosynthesis.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Huaibin Yu, Shuangshuang Wang, Jianjian Huang, Yu Fu, Manfred Wagner, Tanja Weil, Fangrui Zhong, Weining Zhao, Yuzhou Wu
Summary: This article reports the molecular design of a novel multifunctional reagent for light-controlled selective protein labeling. The molecule combines the functionalities of protein-ligand recognition, bioconjugation, ligand cleavage, and photoactivation. By releasing a highly electrophilic o-naphthoquinone methide, the reagent achieves proximity-driven selective labeling with the protein of interest while retaining its native function.
Article
Chemistry, Organic
Yangjinxiu Zhou, Tengfei Pang, Yu Liu, Fangrui Zhong, Guojiao Wu
Summary: We present a highly intriguing and underexplored multi-component reaction involving diazo molecules for polyene formation. This reaction involves coupling of 2,2,2-trifluorodiazoethane and aryl alkynes mediated by iodine under visible light. The reaction provides a straightforward and step-economic access to bistrifluoromethylated 1,3,5-trienes in high stereoselectivity by creating three C=C bonds in a single step under mild conditions.
Article
Chemistry, Analytical
Shuangshuang Wang, Huaibin Yu, Longjie Li, Meizhou Zhang, Yu Fu, Zi'an Lin, Jinsheng Li, Fangrui Zhong, Hongmei Liu, Yuzhou Wu
Summary: We report the development of inhibitory and noninhibitory fluorescent turn-on probes for specific labeling of GPx4 in live cells. These probes allow visualization of GPx4 expression levels and degradation kinetics, and reveal the real-time response of GPx4 to cellular selenium availability. They also have potential applications in predicting the sensitivity of GPx4-related ferroptosis drugs.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Yu Liu, Tengfei Pang, Weijun Yao, Fangrui Zhong, Guojiao Wu
Summary: A visible-light-induced radical gem-iodoallylation reaction was developed for the synthesis of alpha-CF3-substituted homoallylic iodide compounds from CF3CHN2. The reaction showed broad substrate scope, good compatibility with functional groups, and operational simplicity. This protocol provides a convenient and attractive tool for the introduction of CF3 group in radical synthetic chemistry.
Article
Chemistry, Multidisciplinary
Yu Fu, Xiaohong Liu, Yan Xia, Xuzhen Guo, Juan Guo, Junshuai Zhang, Weining Zhao, Yuzhou Wu, Jiangyun Wang, Fangrui Zhong
Summary: Artificial enzymes using light energy to trigger electron transfer reactions have been developed for sustainable biocatalysis. By encoding a benzophenone photocatalyst in a yellow fluorescent protein, we demonstrated efficient biocatalytic hydrodehalogenation and deuterodehalogenation of aryl halides. The metal-free enzyme operates via an unnatural catalytic mechanism and shows substrate generality. We also successfully demonstrated whole cell photobiocatalysis using recombinant Escherichia coli cells that express the artificial enzyme.
Review
Chemistry, Organic
Muhammad Adnan Bashir, Jian Wei, Huifei Wang, Fangrui Zhong, Hongbin Zhai
Summary: Oxidative reactions provide an effective strategy for phenol transformations via quinone intermediates. The structural diversity and sustainable accessibility of quinones still need further exploration.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Huan Guo, Jin Liu, Guojiao Wu, Weijun Yao, Fangrui Zhong
Summary: This study presents the first oxidative [4 + 2] cyclization of pyrocatechuic acid with various substituted styrenes using the cell lysate of multicopper oxidase Mnx. The catalytic activity of Mnx is much higher than other commonly used MCOs, leading to diversely functionalized isochromanones with a TON of over 7700.
Article
Chemistry, Organic
Muhammad Adnan Bashir, Langyu Tang, Longjie Li, Huaibin Yu, Weijun Yao, Guojiao Wu, Fangrui Zhong
Summary: A formal dual C(sp(2))-H cross-dehydrogenative C-O bond formation method was developed, which can efficiently assemble diversely functionalized diaryl ethers. The reaction proceeds under mild conditions with excellent atom and step economy. In addition, a rare C(sp(2))-O bond formation occurs in this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Muhammad Adnan Bashir, Yulong Zhang, Huaibin Yu, Bofei Wang, Weining Zhao, Fangrui Zhong
Summary: A novel family of electron donors benzofuro[2,3-b]indoles were successfully synthesized through a bimetallic catalysis strategy involving CoCl2/Cu(OTf)2, which showed superior efficiency and potential for further research. This method outperformed traditional multi-step synthesis approaches and demonstrated promising photophysical properties for potential applications in deep-blue organic light-emitting diodes.
Article
Chemistry, Organic
Yang Ni, Xiang Wan, Honghua Zuo, Muhammad Adnan Bashir, Yu Liu, Huaibin Yu, Rong-Zhen Liao, Guojiao Wu, Fangrui Zhong
Summary: An efficient iron-catalyzed cross-dehydrogenative aromatic C-H amidation using DDQ as an oxidant under mild conditions is reported, providing a straightforward access to structurally diverse diarylamine derivatives incorporating benzofuran/benzothiophene motifs. Mechanistic studies indicated that a nitrogen-centered anilino radical is involved in the C-N bond formation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
