Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
datasetposted on 2021-03-17, 18:50 authored by Huaifeng Li, Daniel Lupp, Pradip K. Das, Li Yang, Théo P. Gonçalves, Mei-Hui Huang, Marwa El Hajoui, Lan-Chang Liang, Kuo-Wei Huang
The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide–alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal–ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.
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Azideredox-neutralinsightatom-economical featurespurification processazidedensityStaudingertheory calculationsbase-metal nickel PN 3 pincer catalystmethodologywaste-freecooperationphosphineimine formationpathwayRedox-Neutral Iminationtoolnon-metaldifficultySustainablemultistep procedureiminationwaste disposal