An Efficient Synthesis of Diaryl Ketones by Iron-Catalyzed Arylation of Aroyl Cyanides

Authors

  • Christophe Duplais,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 089-2180-77680
    Search for more papers by this author
  • Filip Bures Dipl.-Chem.,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 089-2180-77680
    Search for more papers by this author
  • Ioannis Sapountzis Dipl.-Chem.,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 089-2180-77680
    Search for more papers by this author
  • Tobias J. Korn Dipl.-Chem.,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 089-2180-77680
    Search for more papers by this author
  • Gérard Cahiez Prof.,

    1. Laboratoire de Synthèse Organique Sélective et Chimie Organométallique CNRS-UCP-ESCO, 13, Boulevard de L’Hautil, 95092 Cergy-Pontoise cedex, France
    Search for more papers by this author
  • Paul Knochel Prof. Dr.

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 089-2180-77680
    Search for more papers by this author

  • We thank the Fonds der Chemischen Industrie, the DFG and CNRS (financial support to T.J.K.), and Aventis Pharma (Frankfurt a.M., financial support to I.S.) for supporting this research program. We thank BASF AG (Ludwigshafen), Degussa AG (Hanau), and Chemetall GmbH (Frankfurt a. M.) for generous gifts of chemicals.

Abstract

original image

An alternative to acyl chlorides: Iron(III)-catalyzed arylation of aroyl and heteroaroyl cyanides with aryl magnesium reagents (see example in scheme) provides an easy and mild approach to polyfunctionalized diaryl ketones in yields up to 98 %.

Ancillary