Late‐Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis |
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Authors: | Dr Daniel A DiRocco Kevin Dykstra Dr Shane Krska Dr Petr Vachal Donald V Conway Dr Matthew Tudge |
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Institution: | 1. Department of Process Chemistry, Merck Research Laboratories, 90 E. Scott Ave., Rahway, NJ 07065 (USA);2. Department of Medicinal Chemistry, Merck Research Laboratories, 90 E. Scott Ave., Rahway, NJ 07065 (USA);3. Department of Scientific Engineering and Design, Merck Research Laboratories, 90 E. Scott Ave., Rahway, NJ 07065 (USA) |
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Abstract: | The direct C? H functionalization of heterocycles has become an increasingly valuable tool in modern drug discovery. However, the introduction of small alkyl groups, such as methyl, by this method has not been realized in the context of complex molecule synthesis since existing methods rely on the use of strong oxidants and elevated temperatures to generate the requisite radical species. Herein, we report the use of stable organic peroxides activated by visible‐light photoredox catalysis to achieve the direct methyl‐, ethyl‐, and cyclopropylation of a variety of biologically active heterocycles. The simple protocol, mild reaction conditions, and unique tolerability of this method make it an important tool for drug discovery. |
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Keywords: | homogeneous catalysis photoredox catalysis radical reactions visible light |
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