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

2021, Leonard, David K., Li, Wu, Rockstroh, Nils, Junge, Kathrin, Beller, Matthias

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. © 2021