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

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Type
Article
Authors
Li, Huaifeng
Lupp, Daniel cc
Das, Pradip K.
Yang, Li
Goncalves, Theo
Huang, Mei-Hui cc
El Hajoui, Marwa
Liang, Lan-Chang cc
Huang, Kuo-Wei cc
KAUST Department
Biological and Environmental Science and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2021-03-17
Online Publication Date
2021-03-17
Print Publication Date
2021-04-02
Embargo End Date
2022-03-17
Submitted Date
2021-01-27
Permanent link to this record
http://hdl.handle.net/10754/668169

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Abstract
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.1c00379
Sponsors
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 Catalysis
DOI
10.1021/acscatal.1c00379
Additional Links
https://pubs.acs.org/doi/10.1021/acscatal.1c00379
Collections
Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)
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.
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.