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
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, Multidisciplinary
Tao Sheng, Guowei Kang, Zhe Zhuang, Nikita Chekshin, Zhen Wang, Liang Hu, Jin-Quan Yu
Summary: Ligand-enabled ss,γ-dehydrogenation of aliphatic acids is reported, providing a synthetic disconnection and a versatile platform for downstream functionalization. The method exhibits good chemoselectivity and excellent regioselectivity, allowing for late-stage functionalization of bioactive compounds and introduction of covalent warheads into natural product scaffolds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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
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, 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)
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
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
Zhe Chen, Liming Wang, Wenqin Tian, Ying Jin, Xin Qin
Summary: Takemoto's catalysts were used for the enantioselective Friedel-Crafts reaction, resulting in the synthesis of 3-aryl-3-hydroxyl-2-oxindoles with high yields (85-96%) and up to 99% ee. This methodology offers expanded substrate scope compared to previous examples catalyzed by cinchonidine thiourea.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Organic
Zeynep Dilsad Susam, Bilge Deniz Ozcan, Enis Kurtkaya, Erol Yildirim, Cihangir Tanyeli
Summary: In this study, bifunctional quinine-derived organocatalysts were used to catalyze the asymmetric Friedel-Crafts/S(N)2 domino reaction, resulting in enantiomerically enriched products. Density functional theory calculations were also performed to explain the stereoselectivity of the products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Gabriele Lupidi, Benedetta Bassetti, Roberto Ballini, Marino Petrini, Alessandro Palmieri
Summary: A new one-pot synthesis of polysubstituted carbazoles starting from beta-nitro-beta,gamma-unsaturated-ketones and indoles was reported. The process involved a Friedel-Crafts reaction of indoles to nitroolefins supported by 2,2,2-trifluoroethanol (TFE) followed by an acidic-promoted and microwave-assisted intramolecular cyclization, resulting in products with satisfactory to good overall yields (55-78%).
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amjad Ali, Raveena Jajoria, Harish K. Harit, Ravi P. Singh
Summary: In this study, the addition of alpha-ketoamide top-quinone methide initiated by dialkylphosphite in the presence of organic base DBU was explored. The coupling of dialkylphosphites to alpha-ketoamides followed[1,2]-phospha-Brook rearrangement, generating alpha-phosphonyloxy enolates that were subsequently seized by p-quinonemethides. This two-step one-pot 1,6-conjugate addition method provides effective access to a series of isatin-incorporated phosphate-bearing 1,6-adducts with high yield and selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Beata Lukasik, Justyna Kowalska, Sebastian Frankowski, Lukasz Albrecht
Summary: A new umpolung approach has been developed for the asymmetric Friedel-Crafts-type alkylation of electron-poor heteroaromatic systems using hydrazones. The method shows excellent enantioselectivities under aminocatalytic conditions, and also provides a unique strategy for the asymmetric functionalization of electron-poor heteroaromatic systems.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Amir Yeganeh-Salman, Iris Elser, Karlee L. Bamford, Daniel Ebanks, Douglas W. Stephan
Summary: In this study, a catalytic conversion of B-X to B-H bond was achieved using a small amount of [Ph3C](+) as an initiator with Et3SiH. This method was successfully applied to six haloboranes. Additionally, C-F bond activation of benzyl fluorides was observed in the presence of arenes, leading to the formation of Friedel-Crafts products using B-H-9-BBN in the presence of Et3SiH. The protocol provides a simple, cost-effective, and mild route to 1,1-diarylmethanes from benzyl fluorides with high yields (up to 99%).
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Chuan-Wen Lei, Bo-Shuai Mu, Feng Zhou, Jin-Sheng Yu, Ying Zhou, Jian Zhou
Summary: The chemistry of carbocations has witnessed significant advances over the past 120 years, with current research focused on developing catalytic asymmetric reactions to overcome the intrinsic instability and high reactivity of prochiral carbocationic intermediates. Highly enantioselective protocols evolving prochiral carbocationic intermediates have been achieved through various strategies.
CHEMICAL COMMUNICATIONS
(2021)