In 2022,Pan, Pan; Liu, Shihan; Lan, Yu; Zeng, Huiying; Li, Chao-Jun published an article in Chemical Science. The title of the article was 《Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex》.Electric Literature of C6H4ClI The author mentioned the following in the article:
A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides RI (R = Ph, naphthalen-1-yl, thiophen-3-yl, 4-phenylmorpholine, etc.) with hydrazones R1CH=NNH2 (R1 = Ph, naphthalen-1-yl, pyridin-2-yl, 2H-1,3-benzodioxol-5-yl, etc.) 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 Me, 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. In the experiment, the researchers used many compounds, for example, 1-Chloro-3-iodobenzene(cas: 625-99-0Electric Literature of C6H4ClI)
1-Chloro-3-iodobenzene(cas: 625-99-0) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.Electric Literature of C6H4ClI
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com