Premium
Amine‐Triggered 6π‐Electrocyclization–Aromatization Cascade of Ynedienamines
Author(s) -
Li Xijian,
Yu Huidong,
Huang Yong
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601146
Subject(s) - aromatization , chemistry , protonation , electrophile , iminium , cascade , amine gas treating , redox , photochemistry , organic chemistry , catalysis , ion , chromatography
An unprecedented 6π‐electrocyclization–aromatization cascade reaction of ynedienamines is described. The electron‐rich ynedienamine is converted by γ‐protonation to an electrophilic allenyl iminium species which is susceptible to amine addition generating a highly electron‐rich triene intermediate. The 6π‐electrocyclization is accelerated by three electron‐donating substituents in a captodative manner. Subsequent redox‐neutral aromatization allows the direct synthesis of 1,3‐diaminobenzenes from readily available ynedienamines.