Radical C−N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent.
- Resource Type
- Article
- Authors
- Ma, Yuanhong; Pang, Yue; Chabbra, Sonia; Reijerse, Edward J.; Schnegg, Alexander; Niski, Jan; Leutzsch, Markus; Cornella, Josep
- Source
- Chemistry - A European Journal. 3/23/2020, Vol. 26 Issue 17, p3738-3743. 6p.
- Subject
- *AROMATIC amines
*BORYLATION
*ARYL radicals
*SCISSION (Chemistry)
*AMINO group
*AMINES
- Language
- ISSN
- 0947-6539
Herein, we report a radical borylation of aromatic amines through a homolytic C(sp2)−N bond cleavage. This method capitalizes on a simple and mild activation via a pyrylium reagent (ScPyry‐OTf) thus priming the amino group for reactivity. The combination of terpyridine and a diboron reagent triggers a radical reaction which cleaves the C(sp2)−N bond and forges a new C(sp2)−B bond. The unique non‐planar structure of the pyridinium intermediate, provides the necessary driving force for the aryl radical formation. The method permits borylation of a wide variety of aromatic amines indistinctively of the electronic environment. [ABSTRACT FROM AUTHOR]