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Issue 29, 2016
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BODIPY catalyzed amide synthesis promoted by BHT and air under visible light

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Abstract

A novel and efficient protocol for the synthesis of amides is reported which employs a BODIPY catalyzed oxidative amidation reaction between aromatic aldehydes and amines under visible light. Compared with the known Ru or Ir molecular catalysts and other organic dyes, the BODIPY catalyst showed higher reactivity toward this reaction. Mechanistic studies reveal that dioxygen could be activated through an ET and a SET pathway, forming active peroxides in situ, which are vital for the key step of the reaction, i.e. the oxidation of hemiaminal to amide. The broad substrate scope and mild reaction conditions make this reaction practically useful and environmentally friendly for the synthesis of amide compounds.

Graphical abstract: BODIPY catalyzed amide synthesis promoted by BHT and air under visible light

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Publication details

The article was received on 07 Apr 2016, accepted on 23 Jun 2016 and first published on 23 Jun 2016


Article type: Paper
DOI: 10.1039/C6OB00736H
Org. Biomol. Chem., 2016,14, 7028-7037

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    BODIPY catalyzed amide synthesis promoted by BHT and air under visible light

    X. Wang, S. Yu, C. Wang, D. Xue and J. Xiao, Org. Biomol. Chem., 2016, 14, 7028
    DOI: 10.1039/C6OB00736H

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