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Ruᴵᴵ-Catalyzed/NH₂-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines

Author:
Chen, Pu, Nan, Jiang, Hu, Yan, Ma, Qiong, Ma, Yangmin
Source:
Organic letters 2019 v.21 no.12 pp. 4812-4815
ISSN:
1523-7052
Subject:
carbon-hydrogen bond activation, catalytic activity, chemical reactions, moieties, quinolines
Abstract:
A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly of highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C–H activation with sulfoxonium ylides as one-carbon coupling partners. Various 2-acylquinolines could be obtained with good yields and excellent functional group tolerance. Moreover, the potential synthetic application of this methodology was exemplified by several chemical transformations.
Agid:
6478225