Issue 12, 2017

Photocatalytic N-formylation of amines via a reductive quenching cycle in the presence of air

Abstract

Photochemical N-formylation of amines was performed under simple and mild reaction conditions. Amines are common electron donors in reductive photocatalysis, which then typically decompose after donating an electron to the photocatalyst. We have found that these oxidized amines can be utilized to give N-formamides in the presence of air without additional formylating agents. The reaction proceeds via the in situ formation of enamines. Oxygen (air) is necessary for the reaction to occur as it regenerates the photocatalyst forming superoxide radical anions as crucial intermediates involved in the reaction.

Graphical abstract: Photocatalytic N-formylation of amines via a reductive quenching cycle in the presence of air

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2017
Accepted
23 Feb 2017
First published
24 Feb 2017

Org. Biomol. Chem., 2017,15, 2536-2540

Photocatalytic N-formylation of amines via a reductive quenching cycle in the presence of air

T. Ghosh, A. Das and B. König, Org. Biomol. Chem., 2017, 15, 2536 DOI: 10.1039/C7OB00250E

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