Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines
- Resource Type
- Article
- Authors
- Xu, Ya-Nan; Zhu, Meng-Zeng; Lin, Yu-Kun; Tian, Shi-Kai
- Source
- Organic Letters; September 2019, Vol. 21 Issue: 17 p7169-7173, 5p
- Subject
- Language
- ISSN
- 15237060; 15237052
An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C–N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts, delivering sterically hindered aromatic amines in moderate to excellent yields with extremely high regioselectivity. Preliminary mechanistic studies permitted successful identification of π-benzylpalladium complexes and γ-vinyl allylic amines as key intermediates. This study paves the way for the use of benzylic ammonium salts in the aromatic substitution reactions.