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

doi:10.1021/acscatal.1c00379

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 journal › Article › peer-review

15 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4071-4076
Number of pages	6
Journal	ACS Catalysis
DOIs	https://doi.org/10.1021/acscatal.1c00379
State	Published - 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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10.1021/acscatal.1c00379

https://repository.kaust.edu.sa/bitstream/10754/668169/1/acscatal.1c00379.pdf

Cite this

@article{974dfdaa6ed140a1ba60b32995dc26e1,

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

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.",

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

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.",

year = "2021",

month = mar,

day = "17",

doi = "10.1021/acscatal.1c00379",

language = "English (US)",

pages = "4071--4076",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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AU - Li, Huaifeng

AU - Lupp, Daniel

AU - Das, Pradip K.

AU - Yang, Li

AU - Goncalves, Theo

AU - Huang, Mei-Hui

AU - El Hajoui, Marwa

AU - Liang, Lan-Chang

AU - Huang, Kuo-Wei

N1 - 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.

PY - 2021/3/17

Y1 - 2021/3/17

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/668169

UR - https://pubs.acs.org/doi/10.1021/acscatal.1c00379

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DO - 10.1021/acscatal.1c00379

M3 - Article

SN - 2155-5435

SP - 4071

EP - 4076

JO - ACS Catalysis

JF - ACS Catalysis

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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