Issue 24, 2022

Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex

Abstract

A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed that the association of the hydrazone anion with aryl halides formed an electron donor–acceptor complex, which when excited with visible light generated an aryl radical via single-electron transfer.

Graphical abstract: Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Apr 2022
Accepted
23 May 2022
First published
23 May 2022
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., 2022,13, 7165-7171

Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex

P. Pan, S. Liu, Y. Lan, H. Zeng and C. Li, Chem. Sci., 2022, 13, 7165 DOI: 10.1039/D2SC01909D

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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