A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

Holly Jane Davis; Daniel Häussinger; Thomas R Ward; Yasunori Okamoto

doi:10.1002/cctc.202000488

A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

ChemCatChem. 2020 Sep 17;12(18):4512-4516. doi: 10.1002/cctc.202000488. Epub 2020 Jul 22.

Authors

Holly Jane Davis¹, Daniel Häussinger², Thomas R Ward¹, Yasunori Okamoto^{1

3}

Affiliations

¹ Department of Chemistry University of Basel Mattenstrasse 24a BRP 1096 Rosental CH-4058 Basel Switzerland.
² Department of Chemistry University of Basel St. Johanns-Ring 19 CH-4056 Basel Switzerland.
³ Frontier Research Institute for Interdisciplinary Sciences Tohoku University 6-3 Aramaki aza Aoba Aoba-ku Sendai 980-8578 Japan.

Abstract

Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2',3'-c]phenazine)Cl]⁺ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H₂O₂ generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.

Keywords: Biomimetic; Organometallic complex; Photocatalysis; Reaction-in-water; Selective-dehydrogenation.