Dual Roles of Azide: Dearomative Dimerization of Furfuryl Azides.
J Org Chem
; 87(15): 10185-10198, 2022 08 05.
Article
in En
| MEDLINE
| ID: mdl-35864566
ABSTRACT
A dearomative dimerization of furfuryl azides for the construction of furfuryl triazoles is developed. As a rare leaving group, azide is capable of initiating the generation of a furfuryl cation under the Lewis acid-catalyzed conditions, followed by reacting with the other azide to realize an intermolecular [3 + 2] cycloaddition/furan ring-opening cascade. By extending the reaction time, a fragmentation reaction of resulting furfuryl triazoles occurs to afford 1H-triazoles in high yield. Control studies demonstrated that key furfuryl cations also can be obtained from furfuryl triazoles. Furthermore, a chemoselective cross-cycloaddition can be achieved between furfuryl azides and a benzyl azide.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Azides
/
Alkynes
Language:
En
Journal:
J Org Chem
Year:
2022
Document type:
Article
Affiliation country: