Chiral bis(pyrazolyl)methane copper(I) complexes and their application in nitrene transfer reactions

Zeitschrift für Naturforschung B, vol. 76, pp. 835–847

Abstract

Abstract In this study, chiral bis(pyrazolyl)methane copper(I) acetonitrile complexes were applied to generate two novel terminal copper tosyl nitrene complexes with the nitrene generating agent SPhINTs in dichloromethane at low temperatures. The syntheses of the chiral bis(pyrazolyl)methane ligands are based on pulegone and camphor, members of the natural chiral pool. The chiral copper(I) acetonitrile complexes were applied as catalysts in the copper nitrene mediated aziridination reaction of different styrene derivatives and the C–H amination of various substrates. The reactions afforded good yields, but low enantiomeric excess under mild conditions. The nitrene species have been characterized with UV/Vis and EPR spectroscopy and the products of the decay by ESI mass spectrometry.

Authors 5

1. Fabian Thomas Aachen Institute of Inorganic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Inorganic Chemistry, RWTH Aachen University , Landoltweg 1a, 52074 Aachen , Germany

2. Dominik Steden Aachen Institute of Inorganic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Inorganic Chemistry, RWTH Aachen University , Landoltweg 1a, 52074 Aachen , Germany

3. Alexander Eith Aachen Institute of Inorganic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Inorganic Chemistry, RWTH Aachen University , Landoltweg 1a, 52074 Aachen , Germany

4. Alexander Hoffmann Aachen Institute of Inorganic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Inorganic Chemistry, RWTH Aachen University , Landoltweg 1a, 52074 Aachen , Germany

5. Sonja Herres‐Pawlis corresponding Aachen Institute of Inorganic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Inorganic Chemistry, RWTH Aachen University , Landoltweg 1a, 52074 Aachen , Germany