Palladium-catalysed selective oxidative amination of olefins with Lewis basic amines.
Journal
Nature chemistry
ISSN: 1755-4349
Titre abrégé: Nat Chem
Pays: England
ID NLM: 101499734
Informations de publication
Date de publication:
10 2022
10 2022
Historique:
received:
15
06
2021
accepted:
19
07
2022
pubmed:
2
9
2022
medline:
30
9
2022
entrez:
1
9
2022
Statut:
ppublish
Résumé
Amines are prominent in natural products, pharmaceutical agents and agrochemicals. Moreover, they are synthetically valuable building blocks for the construction of complex organic molecules and functional materials. However, amines, especially aliphatic and aromatic amines with free N-H bonds, tend to coordinate with transition metals and deactivate the catalyst, posing a tremendous challenge to applying Lewis basic amines in the amination of olefins. Here we present an example of oxidative amination of simple olefins with various Lewis basic amines. The combination of a palladium catalyst, 2,6-dimethyl-1,4-benzoquinone and a phosphorous ligand leads to the efficient synthesis of alkyl and aryl allylamines. A series of allylamines were obtained with good yields and excellent regio- and stereoselectivities. Intramolecular amination to synthesize tetrahydropyrrole and piperidine derivatives was also realized. Mechanistic investigations reveal that the reaction undergoes allylic C(sp
Identifiants
pubmed: 36050380
doi: 10.1038/s41557-022-01023-x
pii: 10.1038/s41557-022-01023-x
doi:
Substances chimiques
Agrochemicals
0
Alkenes
0
Amines
0
Lewis Bases
0
Ligands
0
Pharmaceutical Preparations
0
Piperidines
0
Palladium
5TWQ1V240M
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1118-1125Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer Nature Limited.
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