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Facile Access to Multiaryl‐1 H ‐pyrrol‐2(3 H )‐ones by Copper/TEMPO‐Mediated Cascade Annulation of Diarylethanones with Primary Amines and Mechanistic Insight
Author(s) -
Wang Xing,
Zhang ChenYang,
Tu HaiYang,
Zhang AiDong
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601178
Subject(s) - annulation , chemistry , cascade , primary (astronomy) , substituent , quaternary carbon , combinatorial chemistry , cascade reaction , copper , luminescence , organic chemistry , catalysis , optoelectronics , physics , chromatography , astronomy , enantioselective synthesis
A straightforward approach to an array of multiaryl‐1 H ‐pyrrol‐2(3 H )‐ones featuring an α‐diarylated all‐carbon quaternary center was developed by using diarylethanones and primary amines as the raw materials. A complete mechanism involving a CuO/TEMPO‐mediated multistep cascade process with an inherent delicate balance of substituent electronic effect is proposed. Moreover, this class of multiaryl β,γ‐unsaturated γ‐lactams demonstrates an intriguing aggregation‐induced emission effect valuable for potential application in developing luminescent materials.