Iron‐Mediated Electrophilic Amination of Organozinc Halides using Organic Azides

Graßl, Simon; Singer, Johannes und Knochel, Paul (2020): Iron‐Mediated Electrophilic Amination of Organozinc Halides using Organic Azides. In: Angewandte Chemie International Edition, Bd. 59, Nr. 1: S. 335-338

Abstract

A wide range of alkyl‐, aryl‐ and heteroarylzinc halides were aminated with highly functionalized alkyl, aryl, and heterocyclic azides. The reaction proceeds smoothly at 50 °C within 1 h in the presence of FeCl3 (0.5 equiv) to furnish the corresponding secondary amines in good yields. This method was extended to peptidic azides and provided the arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of pharmaceutical relevance using this iron‐mediated electrophilic amination as the key step.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1433-7851
• Sprache: Englisch