Aerobic iron-catalyzed site-selective C(sp3)–C(sp3) bond cleavage in N-heterocycles

Abstract

The kinetic and thermodynamic stability of C(sp3)–C(sp3) bonds makes the site-selective activation of these motifs a real synthetic challenge. In view of this, herein a site-selective method of C(sp3)–C(sp3) bond scission of amines, specifically morpholine and piperazine derivatives, using a cheap iron catalyst and air as a sustainable oxidant is reported. Furthermore, a statistical design of experiments (DoE) is used to evaluate multiple reaction parameters thereby allowing for the rapid development of a catalytic process.

Keywords

• Iron
• Oxidation
• C–C bond activation
• Design of experiments