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, Vol. 21, No. 2: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English