Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Type
ArticleAuthors
Li, HuaifengLupp, Daniel

Das, Pradip K.
Yang, Li
Goncalves, Theo
Huang, Mei-Hui

El Hajoui, Marwa
Liang, Lan-Chang

Huang, Kuo-Wei

KAUST Department
Biological and Environmental Science and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2021-03-17Online Publication Date
2021-03-17Print Publication Date
2021-04-02Embargo End Date
2022-03-17Submitted Date
2021-01-27Permanent link to this record
http://hdl.handle.net/10754/668169
Metadata
Show full item recordAbstract
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.Citation
Li, H., Lupp, D., Das, P. K., Yang, L., Gonçalves, T. P., Huang, M.-H., … Huang, K.-W. (2021). Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction. ACS Catalysis, 4071–4076. doi:10.1021/acscatal.1c00379Sponsors
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.Publisher
American Chemical Society (ACS)Journal
ACS CatalysisAdditional Links
https://pubs.acs.org/doi/10.1021/acscatal.1c00379ae974a485f413a2113503eed53cd6c53
10.1021/acscatal.1c00379
Scopus Count
Except where otherwise noted, this item's license is described as This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acscatal.1c00379.