In the last decade photoredox catalysis has emerged as an important tool for organic chemists. The mild conditions employed have allowed access to a broad range of synthetic methodologies, in particular radical reactions on otherwise highly sensitive substrates.[1] Of particular interest are the additions onto a double bond.[2] Herein we report a new methodology for the room temperature photoredox catalysed alkoxy- and amino-arylation of styrenes using diaryl-iodonium tetrafluoroborates as aryl radical precursors.[3]This allows the successful regioselective coupling of three disparate components and can be expanded to a wide range of alcohol nucleophiles and water in good yields. Ritter-type reactions have been explored using nitriles as amide synthons. The mild conditions used permit the effective reaction of electron-rich styrenes known to undergo easy polymerisation. Halogen functionalities are also tolerated, which allows further molecular elaboration. Aryl diazonium salts can be successfully employed to expand the scope of the reaction, exploring aryl patterns otherwise not accessible from the diaryl-iodonium salts.[1] Stephenson, C. J. R., et al., Chem. Soc. Rev., 2011  , 40, 102-113; MacMillan, W. C., et al., Chem. Rev., 2013  , 113, 5322-5363[2] a) Akita, M., et al., Angew. Chem. Int. Ed., 2012  , 51, 9567-9571; b) Akita, M., et al., Org. Lett., 2013  , 15, 2136-2139; c) Konig, B., et al., Angew. Chem. Int. Ed., 2014  , 53, 725-728[3] Fumagalli, G., Boyd, S., Greaney, M. F., Org. Lett., 2013  , 15, 4398-4401

Photoredox catalysed oxyarylation and aminoarylation of styrenes

248th National Meeting (2014)

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