Borohydride Ionic Liquids as Reductants of CO 2 in the Selective N-formylation of Amines

Borohydride imidazolium ionic liquids, [IL]BH , used for the first time as reductants in the N-formylation of various amines with CO , provided an excellent yield of formamides. Under the same conditions, 5 bar CO and 80 °C, NaBH produced a mixture of N-formylated and N-methylated products in a rati...

Full description

Saved in:
Bibliographic Details
Published in:ChemSusChem 2024-04, Vol.17 (7), p.e202301120
Main Authors: Pąchalska, Paulina, Skarżyńska, Anna, Matias, Ines A S, Trzeciak, Anna M
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Borohydride imidazolium ionic liquids, [IL]BH , used for the first time as reductants in the N-formylation of various amines with CO , provided an excellent yield of formamides. Under the same conditions, 5 bar CO and 80 °C, NaBH produced a mixture of N-formylated and N-methylated products in a ratio of 1 : 2. An alternative approach, based on the addition of halide imidazolium salts ([IL]Cl or [IL]Br) to the reactions of amine with NaBH and CO , resulted in a significant increase of selectivity to formamide. However, no effect was noted for [IL]BF and [IL]PF . Monitoring the reaction course in time using H NMR brought about new insight into the role of BH in the reduction of CO and the functionalization of amines. The formation of N-methylaniline - borane intermediate was evidenced.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.202301120