Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
17 04 2019
17 04 2019
Historique:
pubmed:
25
3
2019
medline:
7
8
2020
entrez:
26
3
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 30905151
doi: 10.1021/jacs.9b01886
pmc: PMC6996791
mid: NIHMS1551057
doi:
Substances chimiques
Amines
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
6392-6402Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM118176
Pays : United States
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