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Iron‐Mediated Electrophilic Amination of Organozinc Halides using Organic Azides
Author(s) -
Graßl Simon,
Singer Johannes,
Knochel Paul
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201911704
Subject(s) - electrophilic amination , amination , chemistry , alkyl , halide , electrophile , aryl , amine gas treating , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis
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 FeCl 3 (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.