Water-Promoted Ir-Catalyzed Ring-Opening of Oxa(aza)benzonorbornadienes with Fluoroalkylamines.
J Org Chem
; 83(17): 10097-10106, 2018 Sep 07.
Article
em En
| MEDLINE
| ID: mdl-30040416
ABSTRACT
A highly effective water-promoted iridium-catalyzed ring-opening reaction of oxa(aza)benzonorbornadienes with fluoroalkylamines was developed for the synthesis of fluorinated trans-1,2-amino alcohol or diamine derivatives. Tetrabutylammonium iodide (TBAI) was necessary as an additive for excellent yields in the presence of [Ir(COD)Cl]2 catalyst. Fluorinated trans-1,2-amino alcohol or diamine derivatives could be obtained in good to excellent yields (up to 98%) under mild conditions within a shorter period. Another interesting finding was that the addition of water could greatly enhance the ring-opening reaction. In addition, a plausible mechanism for the ring-opening reaction was proposed.
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01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2018
Tipo de documento:
Article