Intermolecular Allene Functionalization by Silver-Nitrene Catalysis.
J Am Chem Soc
; 142(30): 13062-13071, 2020 07 29.
Article
en En
| MEDLINE
| ID: mdl-32590895
ABSTRACT
Under silver catalysis conditions, using [Tp*,BrAg]2 as the catalyst precursor, allenes react with PhIâNTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Año:
2020
Tipo del documento:
Article
País de afiliación:
España