The ubiquitous presence of sp3 C−H bonds in natural feedstock makes them inexpensive, easily accessible, and attractive synthons for the preparation of common and/or complex molecular frameworks in biologically active natural products, pharmaceutics, agrochemicals, and materials. However, the inertness of these bonds due to the high bond dissociation energies and low polarity difference between the carbon and hydrogen atoms makes them challenging reaction partners. Moreover, the desired site-selectivity is often an issue in reactions with multiple analogous sp3 C−H bonds. To overcome these problems, transition metal-catalyzed C−H functionalization has been developed with the assistance of various well-designed directing groups which can coordinate to a metal center to deliver it on a targeted C−H bond through an appropriate spatial arrangement, enabling C−H activation via the formation of a cyclometalated species. However, the requirement of often additional steps for the construction of the directing groups and their subsequent removal after the desired operation severely hampers the efficacy and compatibility of the reactions. A promising solution would be the utilization of a transient ligand which can bind to the substrate and coordinate to the metal center in a reversible fashion. In this way, the directing group is installed, sp3 C−H functionalization occurs, and the directing group is then removed in situ without affecting the substrate function after the catalysis is finished. Overall, the whole process occurs in a single reaction pot. Herein, we are presenting our studies on transition metal-catalyzed transient directing group-enabled C−H functionalization reaction.
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Site-Selective Functionalization of Common Organic Fragments
Published: 17 November 2022 by MDPI in The 26th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: Transition metal, sp3 carbon, C−H functionalization