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Pyrimidopteridine-Catalyzed Hydroamination of Stilbenes with Primary Amines: A Dual Photoredox and Hydrogen Atom Transfer Catalyst

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posted on 06.04.2021, 19:36 authored by Tobias Taeufer, Richy Hauptmann, Firas El-Hage, Thea S. Mayer, Haijun Jiao, Jabor Rabeah, Jola Pospech
The applicability of a heteroaromatic photoredox catalyst in an additive-free photo-mediated hydroamination of stilbenes is described. Initiated by the excitation of a highly potent organic pyrimidopteridine photoredox catalyst (E*­[PrPPT*/PrPPT·] = +2.10 V vs SCE in MeCN), the photo-mediated hydroamination of stilbenes was enabled using unprotected, primary aliphatic, allylic, benzylic amines for the synthesis of various α-phenyl phenethylamine derivatives. Notably, the stereogenic center of α-chiral amines was fully preserved. Both starting materials serve as competent quenching partners. Fluorescence- and competitive fluorescence-quenching experiments as well as electron paramagnetic resonance spectroscopic analysis and density functional theory calculations allowed a plausible reaction mechanism to be deduced.