Issue 11, 2021

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Abstract

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylation via radical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

Graphical abstract: Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Supplementary files

Article information

Article type
Edge Article
Submitted
17 nov 2020
Accepted
28 jan 2021
First published
29 jan 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 4069-4078

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

J. Shon, D. Kim, M. D. Rathnayake, S. Sittel, J. Weaver and T. S. Teets, Chem. Sci., 2021, 12, 4069 DOI: 10.1039/D0SC06306A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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