N-Formylation of amines via trapping of degradation intermediate of ethers

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Vol. 438; p. 114555
• Main Authors: Ramdar, Moosa, Kazemi, Foad, Eskandari, Parvin, Mirzaei, Majid, Kaboudin, Babak, Taran, Zahra
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-04-2023
• Subjects: Amines; Ethers; Formylation; LED irradiation; Photocatalysis; Photochemistry; LED irradiation; Amines; Formylation; Ethers; Photocatalysis; Photochemistry
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2023.114555

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•N-formylation of amines was achieved via the trapping of formic acid formed as photodegradation intermediate of common ethers.•Diglyme, dioxane and THF successfully were used as solvents and formylating agents.•TiO2 was used as photocatalyst for N-formylation of different amines with electron withdrawing and electrondonating groups under sunlight irradiation.•The photochemical formylation reaction of amines was done under visible 400 nm LED irradiation in dioxane.•Ammonium persulfate/dioxane successfully was used as formylation agent of amines in non-photochemical condition.
In this paper, ethers such as dioxane, diglyme and THF were used as new formylating agents in photocatalytic (nano titania, solar light irradiation), photochemical (400 nm LED irradiation) and non-photo-induced (stoichiometric peroxide reagent) conditions. This work is about trapping and using of formic acid as a photodegradation intermediate, which discloses a new idea for the valorization of degradation intermediates to value-added products. The reactions generated the corresponding formamides in good yields under simple and mild conditions.