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

Tamal Kanti Das, Agustin M. Rodriguez Treviño, Sanjay Pandiri, Sini Irvankoski, Juha H. Siitonen, Sara M. Rodriguez, Muhammed Yousufuddin, László Kürti*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
8 Downloads (Pure)

Abstract

Both metal-catalyzed and organocatalytic transfer hydrogenation reactions are widely employed for the reduction of C = O and C N bonds. However, selective transfer hydrogenation reactions of C 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.

Original languageEnglish
Pages (from-to)746-754
JournalGreen Chemistry
Volume25
Issue number2
Early online date4 Jan 2023
DOIs
Publication statusPublished - 21 Jan 2023
MoE publication typeA1 Journal article-refereed

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