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Divergent Late‐Stage (Hetero)aryl C−H Amination by the Pyridinium Radical Cation
Author(s) -
Ham Won Seok,
Hillenbrand Julius,
Jacq Jérôme,
Genicot Christophe,
Ritter Tobias
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810262
Subject(s) - chemistry , amination , pyridinium , aryl , combinatorial chemistry , molecule , substrate (aquarium) , organic chemistry , catalysis , alkyl , oceanography , geology
(Hetero)arylamines constitute some of the most prevalent functional molecules, especially as pharmaceuticals. However, structurally complex aromatics currently cannot be converted into arylamines, so instead, each product isomer must be assembled through a multistep synthesis from simpler building blocks. Herein, we describe a late‐stage aryl C−H amination reaction for the synthesis of complex primary arylamines that other reactions cannot access directly. We show and rationalize through a mechanistic analysis the reasons for the wide substrate scope and the constitutional diversity of the reaction, which gives access to molecules that would not have been readily available otherwise.

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