The Cleavage of a C-C Bond in Cyclobutylanilines by Visible‐Light Photoredox Catalysis: Development of a [4+2] Annulation Method
Document Type
Article - Abstract Only
Publication Date
2015
Keywords
Cyclohexenes, Iridium catalyst, N-aryl cyclobutyl amines, Photocatalysis, Small ring systems
Abstract
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.
Citation
Wang, J., & Zheng, N. (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. https://doi.org/10.1002/anie.201504076
Comments
Principal Investigator: Nan Zheng
Acknowledgements: We thank the University of Arkansas, the Arkansas Bioscience Institute, the National Institutes of Health (NIH) (grant number P30 GM103450) from the National Institute of General Medical Sciences, and NSF Career Award (Award Number CHE‐1255539) for generous support of this research.