Title

The Cleavage of a C-C Bond in Cyclobutylanilines by Visible‐Light Photoredox Catalysis: Development of a [4+2] Annulation Method

Document Type

Article

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.

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.

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