Iridium-catalyzed silylation of unactivated C–H bonds |
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| Institution: | 1. Institute of Research and Development, Duy Tan University, 03 Quang Trung, Da Nang, Viet Nam;2. Ivanovo State University of Chemistry and Technology, Sheremetievskiy Ave., 7, Ivanovo, 153000, Russian Federation;3. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Street, 664033, Irkutsk, Russian Federation;1. EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, UK;2. GSK Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK;1. Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia;2. Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia;3. Institute for Chemistry, Technology and Metallurgy, P.O. Box 815, Njegoseva 12, 11000 Belgrade, Serbia;1. Department of Chemistry and Center for Advanced Scientific Computing and Modeling (CASCaM), University of North Texas, Denton, TX 76203, United States;2. Department of Chemistry, University of California, Berkeley, CA 94720, United States |
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| Abstract: | The functionalization of primary C–H bonds has been a longstanding challenge in catalysis. Our group has developed a series of silylations of primary C–H bonds that occur with site selectivity and diastereoselectivity resulting from an approach to run the reactions as intramolecular processes. These reactions have become practical by using an alcohol or amine as a docking site for a hydrosilyl group, thereby leading to intramolecular silylations of C–H bonds at positions dictated by the presence common functional groups in the reactants. Oxidation of the C–Si bond leads to the introduction of alcohol functionality at the position of the primary C–H bond of the reactant. The development, scope, and applications of these functionalization reactions is described in this minireview. |
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| Keywords: | C–H bond functionalization Silylation Oxidation Iridium Natural product |
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