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
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
Hui Liu, Yingkun Yan, Min Li, Xiaomei Zhang
Summary: By utilizing chiral phosphoric acid as a catalyst, enantioselective aza-Friedel-Crafts reaction between 5-aminoisoxazoles and isatin-derived N-Boc ketimines was achieved, yielding novel 3-isoxazole 3-amino-oxindoles with high yields and moderate to good enantioselectivities. One product's absolute configuration was determined by X-ray crystal structural analysis, and a plausible reaction mechanism was proposed, followed by a successful scale-up reaction. Additionally, the product underwent Suzuki-Miyaura coupling with phenylboronic acid, resulting in moderate yield without affecting the enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
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, Physical
Ryoya Tajima, Takaaki Saito, Takayoshi Arai
Summary: The conventional acid-catalyzed aza-Friedel-Crafts reaction of phenols with imines typically shows ortho-selectivity. However, a chiral bis(imidazolidine) pyridine (PyBidine)-Ni(OAc)(2) catalyst can switch the regioselectivity to para-selectivity. This switch is facilitated by the bulky PyBidine-Ni(OAc)(2) catalyst with a Ph2CHCH2 substituent, resulting in highly para-selective aza-Friedel-Crafts reactions (up to 99:1 para/ortho selectivity).
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, 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
Chemistry, Applied
Meng-Yang Chang, Nai-Chen Hsueh
Summary: Here, we describe the Bi(OTf)(3)-catalyzed Friedel-Crafts-type annulation of sulfonyl o-hydroxyacetophenones with benzofused cycloethers. This single-step strategy produces functionalized dibenzofused medium-size (9-12) oxacycles through the formation of carbon-carbon and carbon-oxygen single bonds. The oxidative application of the resulting oxacycles is also investigated and the chemical structures of the key products are determined using single-crystal X-ray analysis. Water is generated as a byproduct in the overall process.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
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, Physical
Iryna D. Alshakova, Martin Albrecht
Summary: This research presents an efficient catalytic cascade process for the synthesis of triarylmethanes using a novel iridium catalyst. The method achieves efficient C-C coupling through reductive Friedel-Crafts alkylation, with high yields, excellent selectivities, and low iridium loadings. The catalytic activity of the system with hydride-proton coordination is significantly higher than that of other systems, demonstrating high catalytic performance.
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
Chemistry, Organic
Duc Chu, Jonathan A. A. Ellman
Summary: Unprotected, alpha,beta-disubstitutedtryptaminesand phenethylamines can be obtained through a one-pot, metal-free sequence involving in situ formation of aziridinium salts and subsequent Friedel-Crafts reaction with electron-rich (hetero)-arenes. The use of hexafluoroisopropanol as the solvent greatly facilitates both steps. This method is effective for variously substituted indoles and 1,3,5-trimethoxybenzene, as well as cyclic and acyclic alkenes, exhibiting stereospecificity for both (E)- and (Z)-1,2-disubstituted alkenes. Additionally, a diamine can be synthesized via one-pot morpholine addition to an aziridinium salt.
Article
Chemistry, Inorganic & Nuclear
Dipankar Paul, Siddheswar Rudra, Prabin Rahman, Snehadrinarayan Khatua, Mukul Pradhan, Paresh Nath Chatterjee
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Paresh Nath Chatterjee, Sujit Roy
JOURNAL OF ORGANIC CHEMISTRY
(2010)
Article
Chemistry, Organic
Paresh Nath Chatterjee, Sujit Roy
Article
Chemistry, Organic
Paresh Nath Chatterjee, Sujit Roy
Article
Chemistry, Multidisciplinary
Dipankar Paul, Snehadrinarayan Khatua, Paresh N. Chatterjee
Article
Chemistry, Multidisciplinary
Dipankar Paul, Paresh N. Chatterjee
Article
Chemistry, Organic
Dipankar Paul, Apurba Borah, Snehadrinarayan Khatua, Paresh Nath Chatterjee
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Micky Lanster Sawkmie, Dipankar Paul, Gitumoni Kalita, Khushboo Agarwala, Pradip K. Maji, Paresh Nath Chatterjee
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Dipankar Paul, Paresh Nath Chatterjee
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Gitumoni Kalita, Namrata Deka, Dipankar Paul, Gitish K. Dutta, Paresh Nath Chatterjee
Summary: The sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer THP-SO3H exhibited excellent catalytic activity in a challenging dual C-C bond-breaking reaction, leading to high yields of symmetrical triarylmethanes. The metal-free method developed has a wide scope of applicability with various substrates, and the catalyst can be easily recovered and reused for up to five consecutive cycles without significant loss in efficiency.
Article
Chemistry, Organic
Gitumoni Kalita, Sharat Sarmah, Atanu Singha Roy, Paresh Nath Chatterjee
Summary: This study presents a facile method for the synthesis of 2,2-disubstituted-2H-1-benzopyrans using easily accessible tertiary propargylic alcohols and phenolic derivatives. A sulfonated tetraphenylethylene-based hypercrosslinked polymer (THP-SO3H) was used as a heterogeneous organocatalyst. The catalyst can be easily recovered and reused up to five consecutive cycles with minimal loss in catalytic efficiency. The binding interaction of the synthesized benzopyrans with human serum albumin was investigated using fluorescence spectroscopy and molecular docking techniques.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Gitumoni Kalita, Snehadrinarayan Khatua, Paresh Nath Chatterjee
Summary: This study presents a simple protocol using trifluoromethanesulfonic acid (CF3SO3H) as a Bronsted acid catalyst to synthesize conjugated diene-diones from readily available tertiary propargyl alcohols and 1,3-dicarbonyl compounds. The reactions are performed in undried solvents in an air atmosphere, with water as an environmentally friendly byproduct. Preliminary synthetic applications of the conjugated diene-diones in the formation of conjugated dienones and furans are also reported.
Review
Chemistry, Multidisciplinary
Dipankar Paul, Paresh Nath Chatterjee
Summary: This article provides an overview of the application of carbon-based leaving groups in organic transformations, focusing on the cleavage of C-C bonds in unstrained molecules. The review discusses the leaving group aptitude of active methylene compounds, active methyl compounds, and electron-rich arenes, highlighting the wide utility of carbon-based leaving groups for the formation of new C-H, C-N, C-C, C-O, and C-S bonds.
Article
Chemistry, Multidisciplinary
Dipankar Paul, Snehadrinarayan Khatua, Paresh Nath Chatterjee
NEW JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
