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1.
Dr. Yukiko Karuo Dr. Atushi Tarui Dr. Kazuyuki Sato Dr. Kentaro Kawai Dr. Masaaki Omote 《Chemical record (New York, N.Y.)》2023,23(9):e202300029
In recent years, hydrofluorocarbon compounds such as chlorofluorocarbons, hydrochlorofluorocarbons, and 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane) have been used as fluorine-containing building blocks to construct functional fluorine-containing compounds, e. g., polymers, liquid crystals, and medicines. Hydrofluorocarbons promote the formation of reactive fluoroalkyl or fluoroalkenyl species via anionic or radical processes, and these species can act as nucleophiles or electrophiles depending on the reaction conditions. Progress in fluorine chemistry using hydrofluorocarbons in the last 30 years is described in this review and diverse reactions are discussed, including the fluoroalkyl/alkenyl products and proposed mechanisms involved. 相似文献
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《中国化学快报》2022,33(10):4517-4530
Fluoroalkyl-containing organic compounds have exhibited wide applications in the field of pharmaceuticals, agrochemicals and materials science due to their outstanding properties such as biological activity, metabolic stability, lipophilicity, excellent chemical and thermal stability. Therefore, various synthetic strategies have been developed for the construction of fluoroalkyl-containing compounds, using highly active fluorinating reagents and fluorinated building blocks. Recently, the use of easily available and inexpensive trifluoroacetic anhydride (TFAA) and its anhydride analogues has attracted great attention to access numerous fluoroalkyl-containing compounds through cyclization and coupling reactions. In this review, we summarized the recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides as reagents. This review aims to provide a reference for researchers on how to develop new synthetic straregies of fluorine-containing organic compounds and achieve kilograms or even tons preparation of fluorine-containing organic compounds using fluoroalkyl anhydrides. 相似文献
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《中国化学快报》2023,34(1):107578
Nine new fluorine-containing drugs have been approved by the US Food and Drug Administration (FDA) in 2021, which are presented in this review article. These small molecular drugs feature aromatic fluorine, trifluoromethyl and chlorodifluoro groups. The therapeutic areas of these fluorine-containing drugs include multiple myeloma, lymphoma, HIV, chronic heart failure, chronic myeloid leukemia, (ANCA)-associated vasculitis, migraines, von Hippel-Lindau disease, and non-small cell lung cancer. The brief biological activities and the synthetic methods have been discussed in this review for each of these nine drugs. 相似文献
5.
The introduction of fluorine into an organic molecule imparts unique physicochemical properties. Not surprisingly, fluorine is increasingly incorporated into new drugs and agrochemicals. However, aryl fluoride building blocks are only available through synthesis. The ability to cross-couple polyfluoroaromatics selectively could provide a convenient route to functionalized fluoroaromatics. We report herein the first examples of Pt-catalyzed cross-coupling of aryl fluorides. The methylated products can potentially serve as precursors to a wide range of functionalized fluorinated small molecules. 相似文献
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Fluorine has come to be recognized as a key element in materials science: in heat-transfer agents, liquid crystals, dyes, surfactants, plastics, elastomers, membranes, and other materials. Furthermore, many fluorine-containing biologically active agents are finding applications as pharmaceuticals and agrochemicals. Progress in synthetic fluorine chemistry has been critical to the development of these fields and has led to the invention of many novel fluorinated molecules as future drugs and materials. As a result of the electronic effects of fluorine substituents, fluorinated substrates and reagents often exhibit unusual and unique chemical properties, which often make them incompatible with established synthetic methods. Thus, the problem of how to control the unusual properties of compounds with fluorine substituents deserves much attention, so as to promote the design of facile, efficient, and environmentally benign methods for the synthesis of valuable organofluorine targets. 相似文献
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Rueda-Becerril M Sazepin CC Leung JC Okbinoglu T Kennepohl P Paquin JF Sammis GM 《Journal of the American Chemical Society》2012,134(9):4026-4029
The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F(-) or F(+)). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F(?)). A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals. This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom-stabilized radicals. Furthermore, calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations that otherwise would take multiple synthetic steps. 相似文献
8.
Synthetic fluorinated compounds are enormously useful in areas such as materials, agrochemicals, pharmaceuticals and fine chemicals. While methods of electrophilic fluorination have been extensively developed to stereoselectively install fluorine atoms onto molecules, nucleophilic fluorination is a much less explored approach. Recently, several organofluoro reagents have been designed and used as nucleophiles in the asymmetric synthesis of fluorinated compounds, significantly expanding the scope of enantio-enriched fluorine-containing compounds that can be synthesised. Such organofluoro nucleophiles are particularly useful in organocatalytic transformations. In this review, recent advances in the application of organofluoro nucleophiles in organocatalysis are summarised. 相似文献
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The development of diversity-oriented synthesis based on fluorine-containing building blocks has been one of the hot research fields in fluorine chemistry. β-CF3-1,3-enynes, as one type of fluorine-containing building blocks, have attracted more attention in the last few years due to their distinct reactivity. Numerous value-added trifluoromethylated or non-fluorinated compounds which have biologically relevant structural motifs, such as O-, N-, and S-heterocycles, carboncycles, fused polycycles, and multifunctionalized allenes were synthesized from these fluorine-containing building blocks. This review summarizes the most significant developments in the area of synthesis of organofluorine compounds based on β-CF3-1,3-enynes, providing a detailed overview of the current state of the art. 相似文献
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Pawe Lenartowicz Maarten Beelen Maciej Makowski Weronika Wanat Baej Dziuk Pawe Kafarski 《Molecules (Basel, Switzerland)》2022,27(9)
The incorporation of dehydroamino acid or fragments of oxazole into peptide chain is accompanied by a distorted three-dimensional structure and additionally enables the introduction of non-typical side-chain substituents. Thus, such compounds could be building blocks for obtaining novel foldamers and/or artificial enzymes (artzymes). In this paper, effective synthetic procedures leading to such building blocks—tetrapeptides containing glycyldehydroalanine, glycyldehydrophenylalanine, and glycyloxazole subunits—are described. Peptides containing serine were used as substrates for their conversion into peptides containing dehydroalanine and aminomethyloxazole-4-carboxylic acid while considering possible requirements for the introduction of these fragments into long-chain peptides at the last steps of synthesis. 相似文献
11.
Palladium-Catalyzed Arylfluorination of Alkenes: A Powerful New Approach to Organofluorine Compounds
Dr. Attila Márió Remete Dr. Melinda Nonn Prof. Loránd Kiss 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(63):e202202076
Fluorine incorporation into organic molecules is often beneficial to their absorption, distribution, metabolism, and excretion (ADME) properties or bioactivity. As a consequence, organofluorine compounds have become quite common amongst drugs and agrochemicals, and their preparation is a highly important topic in both synthetic organic chemistry and pharmaceutical chemistry. One of the newly developed methods for accessing organofluorine compounds is Pd-catalyzed arylfluorination of alkenes. It is an olefin difunctionalization process that simultaneously introduces an aryl group and a fluorine atom into an alkene framework. This review provides a concise overview of this powerful and versatile method. 相似文献
12.
Gem-dibromomethylarenes are considered as one of the valuable building blocks in the synthetic field because of their broad range of synthetic applications. These synthons serve as useful intermediates in accessing a varied range of (hetero) aromatic frameworks that can act as vital scaffolds in agrochemicals, medicinal chemistry, material sciences, etc. The additional organic transformations that can be performed using these vital reagents highlights its significance in the area of organic synthesis. This review aims at displaying some discoveries and subsequent improvements of this vital intermediate as an important building block in organic transformations. 相似文献
13.
The gem-difluoroalkenes and related compounds have gained much attention from the organic synthetic community due to their widespread applications as versatile fluorinated building blocks for the synthesis of pharmaceuticals, agrochemicals and functional materials. In the past two decades, significant progress has been made to the development of efficient methods for the construction of gem-difluoroalkenes and useful reactions involving the cleavage of CF bond in gem-difluoroalkenes. In this Digest review, these advances in the synthesis and reaction chemistry of gem-difluoroalkenes are summarized, with special emphasis placed on novel synthetic applications of them in recent ten years. 相似文献
14.
Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers
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Dr. Marie‐Charlotte Belhomme Dr. Tatiana Besset Dr. Thomas Poisson Prof. Dr. Xavier Pannecoucke 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(37):12836-12865
Fluorine chemistry is a field undergoing tremendous expansion. Although much attention has been paid to the introduction of the fluorine atom and the CF3 group, less interest has been devoted to the introduction of functionalized fluorinated building blocks, in sharp contrast with the high versatility of the fluorinated products. In this Minireview, the most relevant methods for the introduction of difluoromethylated building blocks are summarized. Access to difluoromethylated arenes, alkenes, and alkynes is highlighted and special attention is paid to explanation of the reaction mechanism. 相似文献
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Prof. Dr. S. V. Ryabukhin D. V. Bondarenko S. A. Trofymchuk Dr. D. A. Lega Prof. Dr. D. M. Volochnyuk 《Chemical record (New York, N.Y.)》2024,24(2):e202300283
Modern organic chemistry is a titan supporting and reinforcing pharmaceutical, agricultural, food and material science products. Over the past decades, the organic compounds market has been evolving to meet all the research demands. In this regard, medicinal chemistry is especially dependent on available chemical space as subtle tuning of the molecule structure is required to create a drug with relevant physicochemical properties and a remarkable activity profile. The recent rapid evolution of synthetic methodology to deploy fluorine has brought fluorinated compounds to the spotlight of MedChem community. And now unique properties of fluorine still keep fascinating more and more as its justified installation into a molecular framework has a beneficial impact on membrane permeability, lipophilicity, metabolic stability, pharmacokinetic properties, conformation, pKa, etc. The backward influence of medicinal chemistry on organic synthesis has also changed the landscape of the latter towards new fluorinated topologies as well. Such complex relationships create a flexible and ever-changing ecosystem. Given that MedChem investigations strongly lean on the ability to reach suitable building blocks and the existence of reliable synthetic methods in this review we collected advances in the chemistry of respectful, but still enigmatic gem-difluorinated aza-heterocyclic building blocks. 相似文献
16.
FAN Xue-Sen ZHANG Xin-Ying 《有机化学》2003,23(Z1):102-102
Quinolines and their derivatives occur in numerous natural products. Many quinolines display interesting physi ological activities and have found attractive applications as pharmaceuticals and agrochemicals as well as being general synthetic building blocks. [1] Many synthetic methods have been developed for quinolines, [2] but due to their great importance, the development of novel synthetic methods remains an active research area. [3] 相似文献
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Zihao Guo Prof. Qiong Yu Yucong Chen Dr. Jie Liu Tao Li Yuhuang Peng Prof. Wenbin Yi 《Chemical record (New York, N.Y.)》2023,23(9):e202300108
Molecules featuring fluorine-containing functional groups exhibit outstanding properties with high density, low sensitivity, excellent thermal stability, and good energetic performance due to the strong electron-withdrawing ability and high density of fluorine. Hence, they play a pivotal role in the field of energetic materials. In light of current theoretical and experimental reports, this review systematically focuses on three types of energetic materials possessing fluorine-containing functional groups F- and NF2- substituted trinitromethyl groups (C(NO2)2F, C(NO2)2NF2), trifluoromethyl group (CF3), and difluoroamino and pentafluorosulfone groups (NF2, SF5) and investigates the synthetic methods, physicochemical parameters, and energetic properties of each. The incorporation of fluorine-containing functional moieties is critical for the development of novel high energy density materials, and is rapidly being adopted in the design of energetic materials. 相似文献
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Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids
The combination of the unique physical and chemical properties of fluorine with proteinogenic amino acids represents a new approach to the design of biologically active compounds including peptides with improved pharmacological parameters. Therefore, the development of routine synthetic methods which enable the effective and selective introduction of fluorine into the desired amino acids from readily available starting materials is of significant synthetic importance. The scope of this critical review is to summarize the most frequently employed strategies for the synthesis of alpha-difluoromethyl and alpha-trifluoromethyl substituted alpha-amino acids (114 references). 相似文献
20.
Rudy Rubini Ilya Ivanov Dr. Clemens Mayer 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(70):16017-16021
Interfacing biocompatible, small-molecule catalysis with cellular metabolism promises a straightforward introduction of new function into organisms without the need for genetic manipulation. However, identifying and optimizing synthetic catalysts that perform new-to-nature transformations under conditions that support life is a cumbersome task. To enable the rapid discovery and fine-tuning of biocompatible catalysts, we describe a 96-well screening platform that couples the activity of synthetic catalysts to yield non-canonical amino acids from appropriate precursors with the subsequent incorporation of these nonstandard building blocks into GFP (quantifiable readout). Critically, this strategy does not only provide a common readout (fluorescence) for different reaction/catalyst combinations, but also informs on the organism's fitness, as stop codon suppression relies on all steps of the central dogma of molecular biology. To showcase our approach, we have applied it to the evaluation and optimization of transition-metal-catalyzed deprotection reactions. 相似文献