Ionic Liquid (IL) as an Effective Medium for the Highly Efficient Hydroacylation Reaction of Aldehydes with Azodicarboxylates

Abstract

Abstract:The highly efficient hydroacylation reaction of aldehydes with azodicarboxylates has been carried out in the ionic liquid,1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,. The products were readily separated by extraction from the reaction medium and the ionic liquid could be recycled up to 8 times and the yields of the reactions were not affected. Compared to conventional solvents, high yields were achieved with aliphatic saturated aldehydes, and the reaction can be conducted under normal to mild conditions without the use of a catalyst.

Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media

“…31 Consequently, we hypothesized that the hydrazination of imidazo[1,2-a]pyridine with DEAD fell into the iron/TBHP catalyzing oxidative radical reaction mechanism. To confirm our suspicion, a control experiment was conducted without the oxidant, TBHP.…”

A Practical and Highly Efficient Hydroacylation Reaction of Azodicarboxylates with Aldehydes in Water

“…11 Carrying out the above reaction in water would be of tremendous benefit, from a green chemistry perspective, and in this communication, we wish to report the hydroacylation reaction of azodicarboxylates with aldehydes without the use of a catalyst. The reaction in this study is conducted under mild reaction conditions in the presence of water.…”

Synthetic Approaches to Acyl Hydrazides and Their Use as Synthons in Organic Synthesis

“…The growing need for performing reactions without the use of metals, led many research groups in an effort to detect new, more environmentally friendly synthetic pathways for the synthesis of acyl hydrazides. An alternative approach was presented in 2009 from Ni and Headley, 15 who proposed the use of Room Temperature Ionic Liquids (RTILs) for the hydroacylation of azodicarboxylates. RTILs, due to their chemical and physical properties, 16 present some important advantages as reaction media, such as high solubility of many organic compounds and the ability of being easily recyclable.…”

“…17 Utilizing this synthetic pathway, the authors managed to maintain excellent yields in aliphatic aldehydes (Scheme 10) and also improved the yields of unsaturated and aromatic substrates, compared to their previous work. 15…”