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      Palladium-catalyzed allylic alkylation dearomatization of β-naphthols and indoles with gem-difluorinated cyclopropanes

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          Abstract

          A palladium-catalyzed allylic alkylation dearomatization of β-naphthols and indoles with gem-difluorinated cyclopropanes has been developed for the first time.

          Abstract

          A palladium-catalyzed allylic alkylation dearomatization of β-naphthols and indoles with gem-difluorinated cyclopropanes has been developed. This reaction provided an efficient route to access 2-fluoroallylic β-naphthalenones and indolenines bearing quaternary carbon centers in good yields with high Z-selectivity via C–C bond activation, C–F bond cleavage and the dearomatization process, benefiting from the wide substrate scope and good functional group tolerance. Moreover, 2-fluoroallylic furanoindoline and pyrroloindolines were achieved in good efficiency via cascade allylic alkylation, dearomatization and cyclization processes in the presence of Et 3B.

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          Fluorine in medicinal chemistry.

          Sophie Purser, Peter R. Moore, Steve Swallow … (2008)
          It has become evident that fluorinated compounds have a remarkable record in medicinal chemistry and will play a continuing role in providing lead compounds for therapeutic applications. This tutorial review provides a sampling of renowned fluorinated drugs and their mode of action with a discussion clarifying the role and impact of fluorine substitution on drug potency.
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            Fluorine in pharmaceuticals: looking beyond intuition.

            K. Müller, C. Faeh, F Diederich (2007)
            Fluorine substituents have become a widespread and important drug component, their introduction facilitated by the development of safe and selective fluorinating agents. Organofluorine affects nearly all physical and adsorption, distribution, metabolism, and excretion properties of a lead compound. Its inductive effects are relatively well understood, enhancing bioavailability, for example, by reducing the basicity of neighboring amines. In contrast, exploration of the specific influence of carbon-fluorine single bonds on docking interactions, whether through direct contact with the protein or through stereoelectronic effects on molecular conformation of the drug, has only recently begun. Here, we review experimental progress in this vein and add complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank.
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              Introduction of fluorine and fluorine-containing functional groups.

              Theresa Liang, Constanze N. Neumann, Tobias Ritter (2013)
              Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo- and transition-metal catalysis. The most challenging transformation remains the formation of the parent C-F bond, primarily as a consequence of the high hydration energy of fluoride, strong metal-fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost-efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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                Author and article information

                Contributors
                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: February 4 2021
                Publication date (Electronic): 2021
                Volume: 57
                Issue: 10
                Pages: 1262-1265
                Affiliations
                [1 ]State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry
                [2 ]School of Pharmacy
                [3 ]China Pharmaceutical University
                [4 ]Nanjing 210009
                [5 ]P. R. China
                Article
                DOI: 10.1039/D0CC07529A
                SO-VID: eb002421-8f01-4bbf-83ff-8642226d9d03
                Copyright © © 2021
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                http://rsc.li/journals-terms-of-use

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