Get access

Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion

Authors

  • Tjøstil Vlaar,

    1. Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    Search for more papers by this author
  • Razvan C. Cioc,

    1. Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    Search for more papers by this author
  • Pieter Mampuys,

    1. Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium)
    Search for more papers by this author
  • Prof. Dr. Bert U. W. Maes,

    Corresponding author
    1. Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium)
    • Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium)
    Search for more papers by this author
  • Prof. Dr. Romano V. A. Orru,

    Corresponding author
    1. Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    • Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    Search for more papers by this author
  • Dr. Eelco Ruijter

    Corresponding author
    1. Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    • Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    Search for more papers by this author

  • This work was financially supported by The Netherlands Organization for Scientific Research (NWO) by means of a TOP grant to R.V.A.O, and by the Hercules Foundation. We thank Elwin Janssen for technical assistance, Sanne Bouwman for HRMS measurements, and Dr. Andreas W. Ehlers for NMR spectroscopic measurements.

Abstract

original image

O2 rein, H2O raus: Verschiedene Diamine und verwandte Bisnucleophile reagieren in einer oxidativen Insertion von Isocyanid mit Pd(OAc)2 (1 Mol-%) als Katalysator und O2 als eigentlichem Oxidans zu einer Reihe medizinisch relevanter N-Heterocyclen. Der Nutzen dieser nachhaltigen Methode wird anhand der formalen Synthese der Antihistamine Astemizol und Norastemizol demonstriert.

Ancillary