Silver(I) Promoted the C4-H Bond Phosphonation of 1-Naphthylamine Derivatives with H-Phosphonates.
J Org Chem
; 86(17): 11519-11530, 2021 09 03.
Article
em En
| MEDLINE
| ID: mdl-34383506
ABSTRACT
A simple and efficient protocol for silver-promoted direct C-H phosphonation of 1-naphthylamine derivatives with H-phosphonates was described. This reaction proceeded smoothly for 1-naphthylamine derivatives at the C4 site, providing a facile and efficient route to 4-phosphonated 1-naphthylamine derivatives. This phosphonation could tolerate a diverse type of functional groups at the pyridinyl and naphthyl moieties. Further functionalization of the phosphonated product was also explored at the C2 and C8 sites, such as fluoridation, methylation, methoxylation, and amination. In addition, DFT studies of the reaction intermediate showed that the most electrophilic reactive site is at the C4 site in the naphthyl ring.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Organofosfonatos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2021
Tipo de documento:
Article