Open Access
Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications
Yu Kawamata
1, 2
,
David Hickey
2, 3
,
Peng Bai
2, 4
,
Longrui Chen
5
,
Qinglong Hou
5
,
Wenhua Qiao
5
,
Koushik Barman
2, 3
,
Martin H. Edwards
2, 3
,
Hugh Nakamura
1
,
Kyle Knouse
1
,
Chuanguang Qin
1
,
Khalyd J. Clay
1
,
Denghui Bao
5
,
Chao Li
1
,
Lauren T Starr
6
,
Carmen Garcia Irizarry
6
,
Neal W. Sach
7
,
Henry S White
2, 3
,
Matt Neurock
2, 4
,
Min Li
2, 3
,
Phil S Baran
1, 2
2
Center for Synthetic Organic Electrochemistry, 315 South 1400 East, Salt Lake City, Utah 84112, United States
|
5
Asymchem Life Science (Tianjin), Tianjin Economic-Technological
Development Zone, Tianjin 300457, China
|
6
Discovery Sciences, Medicine Design, Pfizer Global Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
|
7
Department of Chemistry, La Jolla Laboratories, Pfizer, 10770 Science Center Drive, San Diego, California 92121, United States
|
Publication type: Journal Article
Publication date: 2019-03-24
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
30905151
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.
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318
Total citations:
318
Citations from 2024:
74
(23%)
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GOST
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Kawamata Yu. et al. Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications // Journal of the American Chemical Society. 2019. Vol. 141. No. 15. pp. 6392-6402.
GOST all authors (up to 50)
Copy
Kawamata Yu., Vantourout J. C., Hickey D., Bai P., Chen L., Hou Q., Qiao W., Barman K., Edwards M. H., Garrido Castro A. F., Degruyter J. N., Nakamura H., Knouse K., Qin C., Clay K. J., Bao D., Li C., Starr L. T., Garcia Irizarry C., Sach N. W., White H. S., Neurock M., Li M., Baran P. S. Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications // Journal of the American Chemical Society. 2019. Vol. 141. No. 15. pp. 6392-6402.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jacs.9b01886
UR - https://doi.org/10.1021/jacs.9b01886
TI - Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications
T2 - Journal of the American Chemical Society
AU - Kawamata, Yu
AU - Vantourout, Julien C
AU - Hickey, David
AU - Bai, Peng
AU - Chen, Longrui
AU - Hou, Qinglong
AU - Qiao, Wenhua
AU - Barman, Koushik
AU - Edwards, Martin H.
AU - Garrido Castro, Alberto F
AU - Degruyter, Justine N
AU - Nakamura, Hugh
AU - Knouse, Kyle
AU - Qin, Chuanguang
AU - Clay, Khalyd J.
AU - Bao, Denghui
AU - Li, Chao
AU - Starr, Lauren T
AU - Garcia Irizarry, Carmen
AU - Sach, Neal W.
AU - White, Henry S
AU - Neurock, Matt
AU - Li, Min
AU - Baran, Phil S
PY - 2019
DA - 2019/03/24
PB - American Chemical Society (ACS)
SP - 6392-6402
IS - 15
VL - 141
PMID - 30905151
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Kawamata,
author = {Yu Kawamata and Julien C Vantourout and David Hickey and Peng Bai and Longrui Chen and Qinglong Hou and Wenhua Qiao and Koushik Barman and Martin H. Edwards and Alberto F Garrido Castro and Justine N Degruyter and Hugh Nakamura and Kyle Knouse and Chuanguang Qin and Khalyd J. Clay and Denghui Bao and Chao Li and Lauren T Starr and Carmen Garcia Irizarry and Neal W. Sach and Henry S White and Matt Neurock and Min Li and Phil S Baran},
title = {Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications},
journal = {Journal of the American Chemical Society},
year = {2019},
volume = {141},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jacs.9b01886},
number = {15},
pages = {6392--6402},
doi = {10.1021/jacs.9b01886}
}
Cite this
MLA
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Kawamata, Yu., et al. “Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.” Journal of the American Chemical Society, vol. 141, no. 15, Mar. 2019, pp. 6392-6402. https://doi.org/10.1021/jacs.9b01886.