A mild one-pot transformation of nitroalkanes to ketones or aldehydes via a visible-light photocatalysis–hydrolysis sequence?

Organic & Biomolecular Chemistry Pub Date: 2022-03-30 DOI: 10.1039/D2OB00267A

Abstract

Using a visible-light photoredox catalysis strategy with household decorative blue LEDs and the additives Et3N and DIPEA, as well as the subsequent hydrolysis sequence, a mild one-pot process for the direct transformation of nitroalkanes to the corresponding ketones and aldehydes, constituting a Nef-like reaction, has been developed. It is worth noting that by using an appropriate photocatalyst (e.g., [Ir(dtbbpy)(ppy)2]PF6) and the extra additive Et3N with the combination of DIPEA and Mg(ClO4)2 in i-PrOH (instead of CH3CN), the transformation of nitroalkanes to the corresponding oximes, rather than nitrones, can be markedly more effective. The oximes can then be hydrolyzed to ketones by reaction with CuCl2·2H2O in a pH 7 buffer solution. This process is appealing because of the benefits of efficient conversion, mild conditions, high yields, and general applicability to compounds with a wide range of labile functional groups.

Graphical abstract: A mild one-pot transformation of nitroalkanes to ketones or aldehydes via a visible-light photocatalysis–hydrolysis sequence
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