Issue 5, 2023

One-pot cascade reactions for the synthesis of dinitroalkanes in aqueous buffer

Abstract

Dinitroalkanes are powerful synthetic building blocks because of the versatility of the 1,3-dinitro motif. Here, we show that dinitroalkanes can be synthesized from aliphatic aldehydes in a three-step cascade reaction catalysed by phosphate buffer and the amino acid lysine. We further show that this methodology can be expanded to limited alcohol substrates (1-butanol and 1-pentanol) with the inclusion of a biocatalysed alcohol oxidation. Simultaneous addition of all reagents gives a maximal yield of 52% of 3-(nitromethyl)hexane, derived from 1-butanol and nitromethane, whereas staggering the introduction of the amino acid catalyst and nitromethane substrate boosts the yield to 71% of 3-(nitromethyl)hexane with near-quantitative consumption of the n-butyraldehyde intermediate. Taken together, this work presents a mild synthetic method that couples multi-step catalytic cascades to generate 1,3-dinitroalkanes.

Graphical abstract: One-pot cascade reactions for the synthesis of dinitroalkanes in aqueous buffer

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2022
Accepted
17 Feb 2023
First published
22 Feb 2023

React. Chem. Eng., 2023,8, 1152-1158

Author version available

One-pot cascade reactions for the synthesis of dinitroalkanes in aqueous buffer

K. N. Stewart, K. G. Hawkins, C. M. Andersen and D. W. Domaille, React. Chem. Eng., 2023, 8, 1152 DOI: 10.1039/D2RE00403H

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