AUTHOR=Guo Shiwei , Li Yinghua , Fan Weibin , Liu Zhiqi , Huang Deguang 

TITLE=Copper(II)-Catalyzed Selective CAr-H Bond Formylation: Synthesis of Dialdehyde Aniline

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.891858

DOI=10.3389/fchem.2022.891858

ISSN=2296-2646

ABSTRACT=<p>A simple and efficient method for the synthesis of dialdehyde aniline in good yields (up to 83%) is explored using Cu(OTf)<sub>2</sub> as the catalyst, Selectfluor as the radical initiator, and DMSO as both the carbon and oxygen sources. Experimental studies indicate that the reaction is achieved by the formylation of two C<sub>Ar</sub>-H bonds, first at the para-position and then at the ortho-position. A possible mechanism is proposed, including the thermal homolysis of Selectfluor, the Cu(II)-facilitated formylation of the C<sub>Ar</sub>-H bonds, and the hydrolysis of the amide under alkaline conditions in air atmosphere.</p>