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      Sulfinate-Salt-Mediated Radical Relay Cyclization of Cyclic Ethers with 2-Alkynylbenzonitriles toward 3-Alkylated 1-Indenones

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          The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates.

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            Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay.

            Direct methods for stereoselective functionalization of sp(3)-hybridized carbon-hydrogen [C(sp(3))-H] bonds in complex organic molecules could facilitate much more efficient preparation of therapeutics and agrochemicals. Here, we report a copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C-H bonds into benzylic nitriles. Hydrogen-atom abstraction affords an achiral benzylic radical that undergoes asymmetric C(sp(3))-CN bond formation upon reaction with a chiral copper catalyst. The reactions proceed efficiently at room temperature with the benzylic substrate as limiting reagent, exhibit broad substrate scope with high enantioselectivity (typically 90 to 99% enantiomeric excess), and afford products that are key precursors to important bioactive molecules. Mechanistic studies provide evidence for diffusible organic radicals and highlight the difference between these reactions and C-H oxidations mediated by enzymes and other catalysts that operate via radical rebound pathways.
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              Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential CH and CN Cleavage

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                Author and article information

                Journal
                Chemistry - An Asian Journal
                Chem. Asian J.
                Wiley
                18614728
                May 04 2018
                May 04 2018
                April 10 2018
                : 13
                : 9
                : 1157-1164
                Affiliations
                [1 ]School of Chemical Engineering & Technology; China University of Mining and Technology; Xuzhou 221116 P. R. China
                [2 ]Department of Chemistry; Xuzhou Medical University; Xuzhou 221004 P. R. China
                [3 ]School of Chemistry and Materials Science; Jiangsu Normal University; Xuzhou 221116 P. R. China
                Article
                10.1002/asia.201800211
                9966fa97-cd87-44f9-baf7-e311afed7e10
                © 2018

                http://doi.wiley.com/10.1002/tdm_license_1.1

                http://onlinelibrary.wiley.com/termsAndConditions#vor

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