Sn-Catalyzed Criegee-Type Rearrangement of Peroxyoxindoles Enabled by Catalytic Dual Activation of Esters and Peroxides.
J Org Chem
; 85(5): 3374-3382, 2020 03 06.
Article
en En
| MEDLINE
| ID: mdl-31999928
ABSTRACT
We report here the Sn-catalyzed mild protocol for ring expansion of peroxyoxindoles to afford the series of substituted-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives. In this protocol, we showed the in situ conversion of tert-butyl peroxy compounds into peresters with the aid of external esters, which then underwent the ring-expansion process, and the incipient carbocation was trapped with the alcohol residue generated from the esters. The reaction is also demonstrated in a continuous flow process to afford the rearranged product in 22 min of residence time.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2020
Tipo del documento:
Article
País de afiliación:
India