Affiliation:
1. Department of Chemistry, Guru Ghasidas Vishwavidyalaya (A Central University), Bilaspur- 495009, Chhattisgarh,
India
2. Department of Chemistry, University of North Bengal, Raja Rammohunpur, Darjeeling-734013, West Bengal,
India
Abstract
Background:
Green and sustainable method for the oxidation of aldehydes into acids is
now in demand as carboxylic acids are important and versatile intermediates. In this context, visible
LED light-promoted aerial oxidation can be efficient and greener protocol.
Objective:
Herein, we have demonstrated a visible LED light-promoted efficient and greener protocol
for the aerial oxidation of aromatic aldehydes into corresponding acids in the absence of any additives,
base, catalyst, and oxidant.
Methods:
The oxidation of aromatic aldehydes was irradiated by an LED light at room temperature
under an open atmosphere, monitored by TLC. The rate of oxidation was also monitored using different
LED lights by UV-Vis studies. The products were purified by column chromatography using silica
gel, and the mixture of ethyl acetate/petroleum ether as an eluting solvent and the pure products were
confirmed by their melting point determination and NMR spectroscopic analysis.
Results:
The aldehydes were successfully converted into corresponding acids with good isolated
yields (60-90 %) by this protocol, where blue LED light (l ~ 490 nm) was found to be the best choice.
Conclusion:
The present protocol of aerial oxidation of aromatic aldehydes into corresponding acids
under visible LED light has been carried out in the absence of catalyst, oxidant, base, and any other
additives. The higher isolated yields, no byproduct formation, and neat reaction conditions are the major
advantages of the protocol.
Publisher
Bentham Science Publishers Ltd.
Subject
General Materials Science
Reference58 articles.
1. Liu K-J.; Fu Y-L.; Xie L-Y.; Wu C.; He W-B.; Peng S.; Wang Z.; Bao W-H.; Cao Z.; Xu X.; He W-M.; Green and efficient: Oxidation of aldehydes to carboxylic acids and acid anhydrides with air. ACS Sustain Chem 2018,6(4),4916-4921
2. Bashpa P.; Bijudas K.; Phase transfer catalysed oxidation of benzaldehyde and substituted benzaldehydes by dichromate in organic medium. Int J Chem Stud 2016,4(6),28-30
3. Hunsen M.; Carboxylic acids from primary alcohols and aldehydes by a pyridiniumchlorochromate catalyzed oxidation. Synthesis 2005,15,2487-2490
4. Sedelmeier J.; Ley S.V.; Baxendale I.R.; Baumann M.; KMnO(4)-Mediated oxidation as a continuous flow process. Org Lett 2010,12(16),3618-3621
5. Travis B.R.; Sivakumar M.; Hollist G.O.; Borhan B.; Facile oxidation of aldehydes to acids and esters with oxone. Org Lett 2003,5(7),1031-1034