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
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
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
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, 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, Organic
Marina Briand, Linh D. Thai, Flavien Bourdreux, Nicolas Vanthuyne, Xavier Moreau, Emmanuel Magnier, Elsa Anselmi, Guillaume Dagousset
Summary: Site-selective trifluoromethylation of silyl dienol ethers derived from alpha,ss-unsaturated aldehydes, ketones, and amides was achieved for the first time in the remote gamma position. An unprecedented enantioselective C(sp(3))-H perfluoroalkylation process is disclosed.
Article
Chemistry, Applied
Htet Htet San, Jie Huang, Seinn Lei Aye, Xiang-Ying Tang
Summary: A boron-catalyzed environmentally benign dehydrative Friedel-Crafts alkylation method has been developed for the first time, replacing toxic and unstable methyl vinyl ketone with safer and cheaper beta-hydroxyl ketone. The reaction is easy to operate, has a wide substrate scope, and only water is formed as a by-product.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Weizhi Gu, Jindong Li, Kuiliang Li, Qi Sun, Tong Li, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Mannich reaction of 2-fluoroindanone with ketimine was developed using a chiral copper complex catalyst, resulting in the formation of a chiral tetrahedral center containing fluorine. The reaction yielded a series of fi-fluoroamine derivatives in excellent yields (73-94%) with high diastereoselectivities (>99:1 dr) and enantioselectivities (89-99%). Density functional theory calculations supported the proposed transition state.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lucimara L. Zachow, Mateus Mittersteiner, Helio G. Bonacorso, Marcos A. P. Martins, Nilo Zanatta
Summary: The N-functionalization of 4-amino-2-trifluoromethyl-1H-pyrroles using alkyl halides is reported. The selectivity of the alkylation reaction was highly dependent on the nature of the alkyl halide and the reaction conditions applied. The alkylated products were subjected to CuAAC reactions, which furnished conjugated 1,2,3-triazoles in good yields.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
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, Organic
Kosuke Nakashima, Sumire Hanamura, Aoi Imamura, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
Summary: This study investigates the asymmetric Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated trifluoromethyl ketones using a squaramide organocatalyst. The squaramide organocatalyst efficiently promotes the reaction, yielding products with both indole motif and trifluoromethyl group in high yields and excellent enantioselectivities (up to 99% ee). The transformation of the obtained adduct to a chiral spiro indoline 3-one is also demonstrated.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuanai Fei, Jun Hou, Huiying Song, Mei-li Yang, Pan Lei, Xiayu Ge, Hongbo Wei, Yuanzhen Xu, Weiqing Xie
Summary: An asymmetric Friedel-Crafts alkylation reaction has been developed for the construction of 3-substituted 3'-indolyloxindoles using in situ generated indol-2-one from functionalized 3-bromooxinidole catalyzed by chiral N,N'-dioxide/Ni(BF4)(2). High yields and enantioselectivities (up to 99% ee) were achieved for the synthesis of these compounds. Furthermore, the potential use of the resulting 3-substituted 3'-indolyloxindole as a key intermediate for the formal synthesis of (+)-folicanthine was demonstrated.
EUROPEAN JOURNAL OF ORGANIC 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
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, Abdullah Saleh Alammari, Assem Barakat, Saeed Alshahrani, Matti Haukka, Abdullah Mohammed Al-Majid
Summary: Five new C-2-symmetric chiral ligands were synthesized from enantiopure amino alcohols, and used for Friedel-Crafts asymmetric alkylation. The bis(oxazolinyl)thiophene ligands showed higher efficiency in inducing asymmetric alkylation compared to bis(imidazolinyl)thiophene analogues.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
