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      Hypervalent Iodine(III)-Promoted C3–H Regioselective Halogenation of 4-Quinolones under Mild Conditions

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          Abstract

          A simple and practical protocol for the C3–H regioselective halogenation of 4-quinolones by the action of potassium halide salt and PIFA/PIDA in good to excellent yields was developed. The current approach provides feasible access to the diversity of C3-halgenated 4-quinolones at room temperature with high regioselectivity and good functional group tolerance, from which bioactive compounds can be easily constructed. Moreover, the current method featured eco-friendly, operational convenience and is suitable for halogenation in a gram scale of 4-quinolones in water without sacrificing yields.

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          The medicinal chemist's toolbox for late stage functionalization of drug-like molecules.

          Tim Cernak, Kevin Dykstra, Sriram Tyagarajan … (2016)
          The advent of modern C-H functionalization chemistries has enabled medicinal chemists to consider a synthetic strategy, late stage functionalization (LSF), which utilizes the C-H bonds of drug leads as points of diversification for generating new analogs. LSF approaches offer the promise of rapid exploration of structure activity relationships (SAR), the generation of oxidized metabolites, the blocking of metabolic hot spots and the preparation of biological probes. This review details a toolbox of intermolecular C-H functionalization chemistries with proven applicability to drug-like molecules, classified by regioselectivity patterns, and gives guidance on how to systematically develop LSF strategies using these patterns and other considerations. In addition, a number of examples illustrate how LSF approaches have been used to impact actual drug discovery and chemical biology efforts.
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            Hypervalent iodine reagents as a new entrance to organocatalysts

            Toshifumi Dohi, Yasuyuki Kita (2009)
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              Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation.

              David A. Petrone, Juntao Ye, Mark Lautens (2016)
              The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 29 November 2021
                Publication date Collection: 14 December 2021
                Volume: 6
                Issue: 49
                Pages: 34044-34055
                Affiliations
                [† ]The Hebei Key Laboratory of Analysis and Control of Zoonotic Pathogenic Micro-organism, College of Life Science, Hebei Agriculture University , Baoding, Hebei 071001, People’s Republic of China
                [‡ ]Colleges of Science, Hebei Agriculture University , Baoding, Hebei 071001, People’s Republic of China
                Author notes
                Author information
                https://orcid.org/0000-0003-3102-6628
                Article
                DOI: 10.1021/acsomega.1c05455
                PMC ID: 8675166
                SO-VID: 759a9f41-b41a-42f9-a818-6c93c9a78933
                Copyright © © 2021 The Authors. Published by American Chemical Society
                License:

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 01 October 2021
                Date accepted : 17 November 2021
                Funding
                Funded by: National Natural Science Foundation of China, doi 10.13039/501100001809;
                Award ID: 22077026
                Funded by: State Key Laboratory of North China Crop Improvement and Regulation, Hebei Agricultural University, doi NA;
                Award ID: YJ2020013
                Funded by: Natural Science Foundation of Hebei Province, doi 10.13039/501100003787;
                Award ID: H2020204002
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 ao1c05455
                document-id-new-14 ao1c05455
                ccc-price

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