Issue 2, 2023

Catalyst-free transfer hydrogenation of activated alkenes exploiting isopropanol as the sole and traceless reductant

Abstract

Both metal-catalyzed and organocatalytic transfer hydrogenation reactions are widely employed for the reduction of C[double bond, length as m-dash]O and C[double bond, length as m-dash]N bonds. However, selective transfer hydrogenation reactions of C[double bond, length as m-dash]C bonds remain challenging. Therefore, the chemoselective transfer hydrogenation of olefins under mild conditions and in the absence of metal catalysts, using readily available and inexpensive reducing agents (i.e. primary and secondary alcohols), will mark a significant advancement towards the development of green transfer hydrogenation strategies. Described herein is an unconventional catalyst-free transfer hydrogenation reaction of activated alkenes using isopropanol as an eco-friendly reductant and solvent. The reaction gives convenient synthetic access to a wide range of substituted malonic acid half oxyesters (SMAHOs) in moderate to good yields. Mechanistic investigations point towards an unprecedented hydrogen bond-assisted transfer hydrogenation process.

Graphical abstract: Catalyst-free transfer hydrogenation of activated alkenes exploiting isopropanol as the sole and traceless reductant

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2022
Accepted
29 Dec 2022
First published
04 Jan 2023

Green Chem., 2023,25, 746-754

Author version available

Catalyst-free transfer hydrogenation of activated alkenes exploiting isopropanol as the sole and traceless reductant

T. K. Das, A. M. Rodriguez Treviño, S. Pandiri, S. Irvankoski, J. H. Siitonen, S. M. Rodriguez, M. Yousufuddin and L. Kürti, Green Chem., 2023, 25, 746 DOI: 10.1039/D2GC04315G

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