Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes

By:Shen, Lei; Zhang, Yang ; Zhang, Linlin; Liu, Chuanwang ;Ma, Zhixian ; Liang, Kangjiang ; Xia, Chengfeng

Chinese Chemical Letters

DOI：https://doi.org/10.1016/j.cclet.2023.108742

Published：2024—Apr. 

Abstract

Spectroscopic investigations discovered that the in -situ generated phenylhydrazone anion was significantly bathochromically shifted to visible light region for photoactivation under irradiation. The photoexcited phenylhydrazone anion was potential to reduce aryl iodides via single electron transfer process for the subsequent radical chain reaction. A redox-neutral photochemical carbonylation of aryl iodides was developed on basis of the special spectroscopic features of phenylhydrazone anion. This protocol provided a convenient and efficient synthetic tool for accessing carbonylation products under redox neutral conditions without the need of transition -metals. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.