Small Aromatics Bearing Two Diarylamino Termini: Highly Reducing Organic Photocatalysts

Dedicated to Professor Dennis Curran on the occasion of his 70th birthday.

Abstract

Small aromatics such as anthracene, naphthalene, or benzene bearing two diarylamino termini function as highly reducing organic photocatalysts (OPCs). In particular, the small aromatic core remarkably enhances the reducing power of the catalyst in the excited state. An appropriate combination of an OPC and an electron-accepting fluoroalkylating reagent is the key to successful radical fluoroalkylation. The basic design of the photocatalyst and the photocatalytic fluoroalkylation of olefins are discussed.

1 Introduction

2 Basic Catalyst Design and Photo- and Electrochemical Properties

3 Photocatalytic Reactions of 9,10-Bis(diphenylamino)anthracene Derivatives

4 Photocatalytic Reactions of 1,4-Bis(diphenylamino)naphthalene Derivatives

5 Photocatalytic Reactions of 1,4-Bis(diphenylamino)benzene

6 Summary and Outlook

Key words

photoredox catalysis - organocatalysis - radical reaction - fluoroalkylation - electron transfer - photoreaction

Publication History

Received: 31 May 2023

Accepted after revision: 10 July 2023

Accepted Manuscript online:
10 July 2023

Article published online:
22 August 2023

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