Article
Chemistry, Multidisciplinary
Jialing Zhong, Rihuang Pan, Xufeng Lin
Summary: An enantioselective Friedel-Crafts reaction of cyclic alpha-diaryl N-acyl imines with indolizines catalyzed by a chiral spirocyclic phosphoric acid has been developed, leading to the synthesis of alpha-tetrasubstituted (3-indolizinyl) (diaryl)methanamines with high enantioselectivity under mild conditions.
Article
Chemistry, Organic
Marina A. Borisova, Dmitry S. Ryabukhin, Alexander Yu Ivanov, Irina A. Boyarskaya, Dmitrii A. Shabalin, Lev E. Zelenkov, Elena Yu Schmidt, Boris A. Trofimov, Aleksander V. Vasilyev
Summary: 5-Hydroxy-1-pyrrolines react with arenes in TfOH or H2SO4 to afford 5-aryl-1-pyrrolines, and undergo dehydration in TfOH or H2SO4 to form N-protonated forms of 3H-pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
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, 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
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
Songjin Guo, Jiayi Chen, Mingjun Yi, Liuli Dong, Aijun Lin, Hequan Yao
Summary: A highly efficient synthesis of unsymmetrical 3,3'-diindolylmethanes has been developed by palladium-catalyzed cascade Heck/cyclization reaction, allowing for the formation of one C-N bond, two C-C bonds and two new rings in one-pot. Precursors allenamides and o-ethynylanilines were utilized to generate in situ indole skeletons, and modification of the methylene unit of diindolylmethane was achieved by treatment with oxidant and silyl nucleophiles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Hejiang Luo, Tongxiang Cao, Shifa Zhu
Summary: The metal-guided method described in the text allows for the divergent synthesis of ketone-fused indoles/pyrroles from N-(2-alkynylaryl) lactam, using regioswitchable Friedel-Crafts cyclization of acylium. The method offers wide substrate scopes, high atom economy, and step economy, making it suitable for the synthesis of structure-related bioactive compounds.
CHINESE 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)
Review
Chemistry, Applied
Daniel Gavina, Marcos Escolano, Javier Torres, Gloria Alzuet-Pina, Maria Sanchez-Rosello, Carlos del Pozo
Summary: Substituted and annulated pyrroles containing chiral centers can be accessed through organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. These compounds are interesting due to their natural occurrence and diverse biological activities. In the past two decades, significant synthetic efforts have been made to develop asymmetric transformations involving pyrroles in the FCA reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
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
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, M. Ali, Abdullah Mohammed Al-Majid, Abdullah Saleh Alamary, Saeed Alshahrani, Sammer Yousuf, Muhammad Iqbal Choudhary, Assem Barakat
Summary: The Friedel-Crafts reaction between substituted indoles as nucleophiles with chalcones-based benzofuran and benzothiophene scaffolds was successfully achieved using a highly efficient bimetallic iron-palladium catalyst system, resulting in a series of bis-heteroaryl products with certain anticancer activities.
Article
Biochemistry & Molecular Biology
Qi Li, Xiu-Xia Liang, Wang Zhang, Man-Yi Han
Summary: A novel double Friedel-Crafts reaction of acylsilanes in water is reported, which allows for the synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. The selectivity of the reaction is regulated by the hydrogen bonds in the 5-hydroxyindole, leading to the synthesis of 1-hydroxy-bis(indolyl)methane derivatives.
Article
Biochemistry & Molecular Biology
Ivan A. Shershnev, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: By studying the reaction mechanism of 5,5,5-trichloropent-3-en-2-one in Bronsted superacid CF3SO3H, it was found that a novel class of indene derivatives can be formed.
Article
Biochemistry & Molecular Biology
Mikhail Kalyaev, Dmitry S. Ryabukhin, Marina A. Borisova, Alexander Yu Ivanov, Irina A. Boyarskaya, Kristina E. Borovkova, Lia R. Nikiforova, Julia Salmova, Nikolay Ul'yanovskii, Dmitry S. Kosyakov, Aleksander V. Vasilyev
Summary: The reactions of furan acids and esters with arenes in the presence of the superacid TfOH result in the formation of hydroarylation products. These compounds demonstrate antimicrobial activity against fungi Candida albicans, as well as inhibitory effects on Escherichia coli and Staphylococcus aureus.
