Review
Biochemistry & Molecular Biology
Marre Porre, Gianmarco Pisano, Fady Nahra, Catherine S. J. Cazin
Summary: Research has shown that α-haloketones play a crucial role in the synthesis of complex heterocycles and pharmacological compounds, and efforts have been made to improve their synthetic methods in terms of sustainability.
Article
Chemistry, Organic
Feng Chen, Xiu-Hua Xu, Lingling Chu, Feng-Ling Qing
Summary: A photochemically induced, nickel-catalyzed radical cross-coupling reaction has been developed for the synthesis of alpha-aryl-alpha-trifluoromethyl alcohols. This reaction utilizes a photoinduced charge transfer process between Hantzsch ester and phthalimido trifluoroethanol to generate a radical intermediate for the cross-coupling with aryl bromides. The protocol is mild and operationally simple, without the need for exogenous photocatalysts or stoichiometric metal reductants, and exhibits broad substrate compatibility and excellent functional group tolerance.
Article
Chemistry, Organic
Pai Zheng, Chuan Liu, Qianding Zeng, Yi Zhang, Ying Liu, Jingjing He, Yupian Deng, Song Cao
Summary: A mild and practical Fe-catalyzed hydroxytrifluoromethylation of alpha-(trifluoromethyl)styrenes with CF3SO2Na in the presence of K2S2O8 and air has been developed. The reaction proceeds efficiently at room temperature without beta-fluoride elimination, resulting in good to excellent yields of alpha, beta-bistrifluoromethyl tertiary alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lorenzo Lombardi, Alessandro Cerveri, Riccardo Giovanelli, Marta Castineira Reis, Carlos Silva Lopez, Giulio Bertuzzi, Marco Bandini
Summary: This paper presents a nickel-catalyzed reductive cross-electrophile coupling reaction, which achieves high yields and high functional group tolerance in the arylation of trifluoroacetaldehyde through a solvent-assisted 1,2-Hydrogen Atom Transfer (HAT) process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Shu-Sen Li, Shuo Sun, Jianbo Wang
Summary: The catalytic asymmetric trifluoromethylation of cyclic ketones via a Sc-III/chiral bisoxazoline-catalyzed homologation reaction using 2,2,2-trifluorodiazoethane (CF3CHN2) as the CF3 source is an efficient method to generate chiral alpha-trifluoromethyl cyclic ketones with excellent diastereoselectivity and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Ziping Li, Jia-ao Wang, Si Ma, Zhenwei Zhang, Yongfeng Zhi, Fuchun Zhang, Hong Xia, Graeme Henkelman, Xiaoming Liu
Summary: This article introduces a new type of photoactive two-dimensional covalent organic frameworks (2D-COFs) for efficient solar to chemical energy conversion. The research shows that triazine-based COFs exhibit good activity, substrate flexibility, recyclability, and higher catalytic efficiency under visible-light irradiation. This study is significant for the rational design of photoactive COFs and the development of fluorine chemistry.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2022)
Article
Chemistry, Applied
Swetha Jos, Webster L. Santos
Summary: The synthesis of alpha-trifluoromethylacrylates from alpha-trifluoroborylacrylates via stereoretentive radical trifluoromethylation at room temperature using inexpensive reagents NaSO(2)CF(3) and TBHP resulted in the exclusive formation of the (E)-diastereomer in moderate to good yield. The reaction products were demonstrated to be useful in the synthesis of phenyl-4H-pyran, a potent and selective class of IKCa channel blockers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Tyrchain Mitre Lipon, Ibakyntiew D. Marpna, Kmendashisha Wanniang, O. Risuklang Shangpliang, Badaker M. Laloo, Rishanlang Nongkhlaw, Bekington Myrboh
Summary: The synthesis employs N-bromosuccinimide (NBS) as the brominating agent mediated by selenium dioxide (SeO2) in the presence of p-toluenesulfonic acid (PTSA) monohydrate in toluene to achieve alpha,beta-unsaturated alpha'-bromoketones and alpha,beta-unsaturated alpha',alpha'-dibromo-ketones. Simple adjustment of reaction conditions and molar equivalents of reactants can yield either mono- or dibrominated products in excellent yields. Some of the products synthesized have not been previously reported in the literature.
Article
Chemistry, Multidisciplinary
Chunfang Guo, Zhaolong Liu, Xiangye Li, Xuliang Han, Yueyun Li, Hui Liu, Lizhi Zhang, Xinjin Li, Yunhui Dong
Summary: A mild and efficient method for direct C-H monofluoroalkylation of heteroarenes using easily accessible and inexpensive alpha-fluorocarboxylic acids has been developed. This silver-catalyzed reaction yields mono- and bis-monofluoroalkylated heteroarenes in good yields under mild conditions, with detailed discussion on the solvent effect on the monofluoroalkylation reaction.
CHEMICAL COMMUNICATIONS
(2022)
Editorial Material
Chemistry, Multidisciplinary
Yuzuru Kanda, Seung Youn Hong, Alexander T. Radosevich
Summary: The study introduces novel phosphine-based reagents that can convert complex azines into fluoroalkylated derivatives. This transformation can impact the biologically relevant properties of compounds.
Article
Chemistry, Organic
Peng Zhao, Lingfeng Wang, Xiaoshuang Guo, Jiayi Chen, Yanbo Liu, Lei Wang, Yongmin Ma
Summary: An efficient photochemical strategy for the synthesis of fluorinated nitrogen-containing heterocycles from diazocarbonyl compounds is disclosed. This transformation involves the reaction of fluoroalkyl radicals with alpha-diazoketones under visible light. A wide range of N-heterocycles containing CF3 and perfluoroalkylated groups are successfully constructed in moderate to good yields. This photochemical strategy may serve as a valuable method for the synthesis of complex organofluorides via diazo/fluorine/radical chemistry.
Article
Chemistry, Organic
Lu Gan, Qing Yu, Yunyun Liu, Jie-Ping Wan
Summary: A new method for the synthesis of α-trifluoromethyl ketones has been developed by cleaving the C=C double bond on tertiary enaminones to form a new C-CF3 bond, with the promotion of TBHP and ambient heating. Control experiments show that the reactions proceed via a featured free radical process, and deuterium labeling experiments indicate the involvement of water in product formation by providing hydrogen atoms.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaowei Chen, Wenhui Wei, Chunyang Li, Hongwei Zhou, Baokun Qiao, Zhiyong Jiang
Summary: A modular strategy was reported for accessing remote fluoroalkylated azaarene derivatives and alpha-deuterated analogues, isosteres of many pharmaceutically important compounds. Transformations under sustainable photoredox catalysis platform efficiently yielded valuable products with high yields and substantial deuterium incorporation. The work demonstrated the viability of hydrogen atom transfer of the alpha-sp(3) C-H of electron-withdrawing azaarenes with alkyl radicals.
Article
Chemistry, Multidisciplinary
Jing Qi, Jinhui Xu, Hwee Ting Ang, Bingbing Wang, Nipun Kumar Gupta, Srinivas Reddy Dubbaka, Patrick O'Neill, Xianwen Mao, Yanwei Lum, Jie Wu
Summary: In this study, a novel electrophotochemical approach is presented for the selective trifluoromethylation of (hetero)-arenes using trifluoroacetic acid (TFA) as the CF3 source. The method offers sustainable and environmentally-friendly synthesis of CF3-, CF2H-, and perfluoroalkyl-containing (hetero)-arenes with improved chemoselectivity by light irradiation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yang Li, Cai-Lin Zhang, Wei-Heng Huang, Ning Sun, Meng Hao, Helfried Neumann, Matthias Beller
Summary: The study presents a novel approach for the synthesis of diverse fluorinated beta-lactams in high yields, utilizing an advanced palladium catalyst system with the Ruphos ligand. This method provides a new strategy for the synthesis of antibiotic drugs in medicinal chemistry.
