The Cleavage of a C-C Bond in Cyclobutylanilines by Visible‐Light Photoredox Catalysis: Development of a [4+2] Annulation Method
cyclohexenes, Iridium catalyst, N-aryl cyclobutyl amines, Photocatalysis, Small ring systems
We report the first example of an intermolecular [4+2] annulation of cyclobutylanilines with alkynes enabled by visible‐light photocatalysis. Monocyclic and bicyclic cyclobutylanilines successfully undergo the annulation with terminal and internal alkynes to generate a wide variety of amine‐substituted cyclohexenes including new hydrindan and decalin derivatives with good to excellent diastereoselectivity. The reaction is overall redox neutral with perfect atom economy.
Jiang, W., & Nan, Z. (2015). The cleavage of a C-C bond in cyclobutylanilines by visible-light photoredox catalysis: Development of a [4+2] annulation method. Angewandte Chemie International Edition, 54(39), 11424-11427. doi:10.1002/anie.201504076