Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Summary: A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes, and indole-3-methanamines by a Friedel-Crafts reaction is developed, showing good to excellent yields, broad substrate compatibility, good functional group tolerance, and scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang, Jun Ren
Summary: A highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been achieved using HFIP as a catalyst. The reaction provides efficient synthesis of various N,N-dialkylanilines and their derivatives with alpha-hydroxy carbonyl units under mild conditions. The method has shown great synthetic potential by enabling the facile synthesis of several structurally interesting molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Vladimir T. Abaev, Nicolai A. Aksenov, Dmitrii A. Aksenov, Elena V. Aleksandrova, Alesia S. Akulova, Igor A. Kurenkov, Alexander V. Leontiev, Alexander V. Aksenov
Summary: The Friedel-Crafts reaction of novel 3,5-diarylsubstituted 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones enables the low-cost, one-pot preparation of polycyclic indole derivatives structurally resembling Ergot alkaloids.
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Multidisciplinary
Jia-Qi Wu, Xin-Yuan Wu, Jian-Mei Lu, Qian Shi, Li-Xiong Shao
Summary: In this study, a novel La(III)-based two-dimensional metal-organic framework was synthesized and used as an efficient Lewis acid catalyst for the Friedel-Crafts alkylation reaction. The catalyst exhibited a unique structure, good stability and catalytic activity in acidic and basic environments.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Nicolas Zeidan, Sergiu Bicic, Robert J. Mayer, David Leboeuf, Joseph Moran
Summary: This study demonstrates that HFIP greatly expands the scope of the Bronsted acid-catalyzed hydroarylation of enamides, and acts as a slow-release reservoir for the key cationic intermediate. The reaction is fast and practical, and can prevent the oligomerization of the substrate.
Article
Chemistry, Multidisciplinary
Cunwei Qian, Xian Li, Ming Zhang
Summary: This study reports the first Friedel- Crafts alkylation of indole with alpha, beta-unsaturated ketones catalyzed by arene diazonium tetrafluoroborate salts, and explores the optimal conditions of the reaction. The experimental results show that the optimal conditions include using 10 mol% of 2-(2-bromophenoxy)phenyl diazonium fluoride borate (2) as the catalyst, CH3OH as the solvent, 60 degrees C as the reaction temperature, and 24 hours as the reaction time. Under these optimized conditions, the reaction of indoles with various alpha, beta-unsaturated ketones can proceed smoothly to obtain the intended products (8), with yields ranging from 60% to 92%. The reaction conditions are mild and the reaction operation is simple.
Article
Chemistry, Multidisciplinary
Ning Li, Wenjing Lu, Weizhi Gu, Kuiliang Li, Jindong Li, Yangmian Lu, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Michael/hemiketalization reaction was developed between isatin-derived beta, gamma-unsaturated alpha-ketoesters and 4-hydroxycoumarins in aqueous media. A series of chiral spirooxindole derivatives with an all-carbon quaternary stereogenic center were obtained in high yields (up to 93%) and excellent enantioselectivities (up to 98%).
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Yanshun Li, Mengqi Dong, Nanxing Gao, Guorui Cao, Dawei Teng
Summary: A zinc complex of a new spiroQuinox ligand with a spirocarbon stereogenic center was used for asymmetric Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters. This catalytic system allows for facile synthesis of benzosultam derivatives functionalized with indole substituents, with high yield and excellent enantioselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Engineering, Chemical
Haonan Zhang, Haotian Zhang, Minli Tao, Wenqin Zhang
Summary: The study synthesized three functionalized polyacrylonitrile fiber catalysts through amination and quaternization, and explored their catalytic activity in the Friedel-Crafts alkylation reaction. The results showed that one of the catalysts exhibited the highest catalytic activity in the reaction and had strong recycling performance. Additionally, this catalyst showed excellent catalytic activity for most aromatic aldehydes containing moderate electron donating groups.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Organic
Ran Chen, Qian-Qian Yan, Shao-Jun Hu, Xiao-Qing Guo, Li-Xuan Cai, Dan-Ni Yan, Li-Peng Zhou, Qing-Fu Sun
Summary: By varying the metal/ligand ratio, dinuclear triple helicates or mononuclear pincer complexes can be selectively obtained from the same chiral bis-tridentate ligand, with both complexes demonstrating catalytic properties in asymmetric Friedel-Crafts alkylation reactions due to the presence of open metal sites.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Bei Zhou, Zhuang Ma, Asma M. Alenad, Carsten Kreyenschulte, Stephan Bartling, Matthias Beller, Rajenahally Jagadeesh
Summary: A general method for cobalt-catalysed CH-alkylation of indoles with alcohols is reported, which allows the easy synthesis of substituted and functionalized indoles in good yields. The resulting products are an interesting class of heterocyclic compounds widely used in organic synthesis and medicinal chemistry.
Article
Chemistry, Organic
Menghui Song, Hongyan Zhou, Ganggang Wang, Ben Ma, Yajing Jiang, Jingya Yang, Congde Huo, Xi-Cun Wang
Summary: A new visible-light-promoted transfer hydrogenation of azobenzenes has been developed, with the reactions proceeding smoothly in methanol at ambient temperature in the presence of B(2)pin(2). Azobenzenes with diverse functional groups were reduced to hydrazobenzenes with a high yield of up to 96%. Preliminary mechanistic studies suggest that the hydrogen atom comes from the solvent and the transformation occurs via a radical pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Agriculture, Multidisciplinary
Xiazhen Bao, Xuehui Cao, Yong Yuan, Bo Zhou, Congde Huo
Summary: A highly efficient fluorescence probe CMQ was developed for the detection of sulfur dioxide in foods and biological systems, showing ultrafast response and low detection limit. Additionally, it was successfully applied for imaging in living cells and zebrafish.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Organic
Jun Li, Yong Yuan, Xiazhen Bao, Tongzhi Sang, Jie Yang, Congde Huo
Summary: An intermolecular vicinal O-N difunctionalization reaction of olefins with oxime esters has been developed using energy transfer catalysis.
Article
Chemistry, Organic
Guozhe Guo, Yong Yuan, Xiazhen Bao, Xuehui Cao, Tongzhi Sang, Jiayuan Wang, Congde Huo
Summary: The study presents a novel visible-light induced redox-neutral decarboxylative cross coupling reaction, which successfully synthesized a variety of symmetrical and unsymmetrical 3,3'-bisindolylmethane derivatives from indole-3-acetic acid NHPI esters and indoles. Additionally, the reaction can be easily adapted for the preparation of a wide range of diarylmethane derivatives.
Article
Chemistry, Organic
Jiayuan Wang, Youwan Ye, Tongzhi Sang, Chenxing Zhou, Xiazhen Bao, Yong Yuan, Congde Huo
Summary: A general C(sp3)-H/C(sp3)-H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons is reported, which involves a combination of SET and HAT process.
Article
Chemistry, Applied
Lanlan Ou, Tongzhi Sang, Congde Huo
Summary: We presented a method to access quinoline-oxadiazole heterobiaryls. This method involves the oxidative (4+2)-cyclization/aromatization tandem reaction of N-aryl heteroaryl methanamines with alkenes or alkynes, catalyzed by copper under aerobic condition.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Tongzhi Sang, Chenxing Zhou, Jun Li, Xincong Liu, Yong Yuan, Xiazhen Bao, Xiaolong Zhao, Congde Huo
Summary: We report a visible-light-promoted approach for the anti-Markovnikov hydrooxygenation of unactivated alkenes. The protocol uses a cost-effective, bench-stable, and easy-to-handle oxime ester as the reagent, enabled by energy-transfer catalysis. This methodology exhibits excellent functional group tolerance and mild reaction conditions, making it suitable for the hydroesterification of pharmaceutically relevant molecule-derived alkenes.
Article
Chemistry, Organic
Tongzhi Sang, Jia Liang, Songhai Huang, Guozhe Guo, Jie Yang, Xiazhen Bao, Congde Huo
Summary: A facile and efficient aerobic oxidative (4 + 2)-cyclization/aromatization/lactonizationtandem reaction of N-aryl glycine esters with propargylalcohols to access quinoline-fused lactones is reported. The reactioncan be extended to homopropargylic alcohols too. The transformationis straightforward to perform under mild conditions and scalable,and both reaction components are readily available.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chengxian Hu, Dan Mou, Xi Zhang, Ying Fu, Congde Huo, Zhengyin Du
Summary: A Pd-catalyzed annulation method has been developed for the synthesis of 10H-indolo[1,2-a]indol-10-one derivatives via C-H bond activation and difluorocarbene transfer. The method features high reactivity and moderate to high yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Guozhe Guo, Yong Yuan, Shuocheng Wan, Xuehui Cao, Yali Sun, Congde Huo
Summary: This study demonstrated for the first time that K2S2O8 promoted dehydrative cross-coupling reaction can synthesize a wide range of allyl sulfides, with broad substrate scopes and tolerance to various substrates, possibly involving a radical addition process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Jia Liang, Ying Fu, Xiazhen Bao, Lanlan Ou, Tongzhi Sang, Yong Yuan, Congde Huo
Summary: A new method for preparing alpha-cyano glycine derivatives through catalytic oxidative reaction using a copper catalyst and NFSI oxidant was reported, with broad substrate scope and mild reaction conditions. CuCl acted as a one-electron reductant and transition-metal catalyst, while NFSI served as a one-electron oxidant generating a N-centered radical as a H-abstractor.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jiayuan Wang, Yingpeng Su, Zhengjun Quan, Jun Li, Jie Yang, Yong Yuan, Congde Huo
Summary: This method utilizes a visible-light-mediated aerobic alpha-alkylation reaction of glycine derivatives with alkyl boronic acids in the presence of a Ru/Cu catalyst system to efficiently produce a wide range of complex unnatural alpha-amino-acid derivatives. It features mild reaction conditions and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Pengfei Niu, Jingya Yang, Yong Yuan, Yongxin Zhang, Chenxing Zhou, Xiazhen Bao, Congde Huo
Summary: In this study, a redox-neutral decarboxylative coupling reaction of heteroaryl methylamines with NHPI esters derived from aliphatic carboxylic acids has been developed. By employing a copper complex as a photocatalyst with blue LED irradiation, NHPI esters underwent one-electron reduction and heteroaryl methenamine derivatives underwent one-electron oxidation in one photo-redox catalytic cycle to form radical intermediates, respectively, followed by the recombination of these two radicals to form new C-C bonds. The methodology allows for the transformation of different kinds of heteroaromatic compounds as well as primary, secondary and tertiary alkyl carboxylic acids, and can be scaled up, with NHPI being recoverable and the reaction being conducted in a one-pot in situ activation manner.
Article
Chemistry, Organic
Jingya Yang, Ganggang Wang, Hongyan Zhou, Zhifeng Li, Ben Ma, Menghui Song, Rongxia Sun, Congde Huo
Summary: The visible-light-promoted O-H insertion reaction between 2-pyridones and alpha-aryldiazoacetates proceeds smoothly under mild and catalyst-free conditions, leading to a wide scope of O-alkylated 2-pyridones with perfect selectivity and good functional group tolerance, likely attributed to a photoinduced radical process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Yingpeng Su, Yanan Zhao, Bingbing Chang, Qinqin Ling, Yawei Feng, Xiaolong Zhao, Danfeng Huang, Ke-Hu Wang, Congde Huo, Yulai Hu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
