Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents

Grassl, Simon; Chen, Yi-Hung; Hamze, Clemence; Tuellmann, Carl Phillip und Knochel, Paul (2019): Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents. In: Organic Letters, Bd. 21, Nr. 2: S. 494-497

Abstract

A general preparation of polyfunctional hydroxylamine benzoates from the corresponding secondary amines is reported. This convenient synthesis allows the setup of a late-stage functionalization of various secondary amines, including pharmaceuticals and peptidic derivatives. Thus, a cross-coupling of hydroxylamine benzoates with various alkyl-, aryl-, and heteroaryl-zinc chlorides in the presence of 5 mol % CoCl2 (25 degrees C, 2 h) provides a range of polyfunctional tertiary amines. This method was used to prepare penfluridol and gepirone.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch