Copper(II)-Catalyzed Selective C-H Bond Formylation: Synthesis of Dialdehyde Aniline.

Front Chem

State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, China.

Published: May 2022

AI Article Synopsis

  • A new method is presented for synthesizing dialdehyde aniline with good yields (up to 83%) using Cu(OTf) as a catalyst and Selectfluor as a radical initiator.
  • The reaction process involves formylating two C-H bonds, first at the para-position followed by the ortho-position.
  • A proposed mechanism includes thermal breakdown of Selectfluor, Cu(II)-assisted formylation of C-H bonds, and the hydrolysis of the amide in alkaline conditions.

Article Abstract

A simple and efficient method for the synthesis of dialdehyde aniline in good yields (up to 83%) is explored using Cu(OTf) 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-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-H bonds, and the hydrolysis of the amide under alkaline conditions in air atmosphere.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9171048PMC
http://dx.doi.org/10.3389/fchem.2022.891858DOI Listing

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