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Development and Mechanistic Insights into Nef Reaction for Preparation of Aldehydes Using Singlet Oxygen
Ira Novita Sari1,2, Bobo Yan1, Tatsuya Morozumi3
1Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, N10W5 Sapporo 060-0810, Japan.
None:
The Nef reaction for conversion of nitro compounds to aldehydes is described. Various functional groups, such as ethers, silyl ethers, acetals or esters, were tolerated to give aldehydes in high yields using Cs2CO3 and singlet oxygen as an oxidant. Transformations of nitromethyl groups into hydroxymethyl groups were achieved in a one-pot operation. The mechanism involved in the Nef reaction was studied using ion chromatography and radical scavengers, which resulted in the proposal of two unique reaction pathways.
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