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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Amination of Phenols and Halophenols via Pyridinium-Iridium Dual Photocatalysis
Matthew C Carson1, Cindy R Liu1, Yaning Liu1
1Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
Abstract:
In this study, we present a photochemical method for the amination of phenols (C─H) and halophenols (SNAr), facilitated by dual catalytic pathways involving both Ir(III) photocatalysis and phenol-pyridinium electron donor-acceptor complexation. By incorporating a pyridinium additive, we achieved efficient C─N coupling between phenols and diverse aromatic nitrogen nucleophiles, delivering high yields (up to 99%) across a wide range of substrates, including pharmaceuticals and natural products. We investigate reaction selectivity and substrate compatibility/limitations through a combination of experimental and computational techniques. Moreover, we highlight the synthetic versatility of the amination products through various late-stage functionalizations including the grafting of two different heteroarenes onto one phenol scaffold.
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