Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction

Huaifeng Li, Daniel Lupp, Pradip K. Das, Li Yang, Theo Goncalves, Mei-Hui Huang, Marwa El Hajoui, Lan-Chang Liang, Kuo-Wei Huang

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


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.
Original languageEnglish (US)
Pages (from-to)4071-4076
Number of pages6
JournalACS Catalysis
StatePublished - Mar 17 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-03-22
Acknowledgements: We are grateful for the financial support from the King Abdullah University of Science and Technology (KAUST), the Ministry of Science and Technology of Taiwan (MOST 109-2113-M-110-004), Guangxi Natural Science Foundation of China (No. 2020GXNSFAA297213), and the State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (No. CMEMR2020-A12) in China. The service of Ibex, Shaheen 2 High Performance Computing Facilities was provided by KAUST.

ASJC Scopus subject areas

  • Catalysis


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