Dichromatic Photocatalytic Substitutions of Aryl Halides with a Small Organic Dye

  1. Neumeier, M. 1
  2. Sampedro, D. 1
  3. Májek, M. 1
  4. de la Peña O'Shea, V.A. 3
  5. Jacobi von Wangelin, A. 13
  6. Pérez-Ruiz, R. 3
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 University of Hamburg
    info

    University of Hamburg

    Hamburgo, Alemania

    ROR https://ror.org/00g30e956

  3. 3 Instituto IMDEA Energía
    info

    Instituto IMDEA Energía

    Móstoles, España

    ROR https://ror.org/002tzev63

Revista:
Chemistry - A European Journal

ISSN: 0947-6539

Año de publicación: 2018

Volumen: 24

Número: 1

Páginas: 105-108

Tipo: Artículo

DOI: 10.1002/CHEM.201705326 SCOPUS: 2-s2.0-85035228688 WoS: WOS:000419046600017 GOOGLE SCHOLAR

Otras publicaciones en: Chemistry - A European Journal

Resumen

Photocatalytic bond activations are generally limited by the photon energy and the efficiency of energy and electron transfer processes. Direct two-photon processes provide sufficient energy but the ultra-short lifetimes of the excited states prohibit chemical reactions. The commercial dye 9,10-dicyanoanthracene enabled photocatalytic aromatic substitutions of non-activated aryl halides. This reaction operates under VIS-irradiation via sequential photonic, electronic, and photonic activation of the simple organic dye. The resultant highly reducing excited photocatalyst anion readily effected C−H, C−C, C−P, C−S, and C−B bond formations. Detailed synthetic, spectroscopic, and theoretical studies support a biphotonic catalytic mechanism. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim