Iodonium Ion-Induced Cyclization and Aryl Migration of ortho-Hydroxystilbenes for the Synthesis of 3-Aryl-2,3-dihydrobenzofuran.
J Org Chem
; 88(16): 11460-11472, 2023 Aug 18.
Article
em En
| MEDLINE
| ID: mdl-37526470
ABSTRACT
A facile and versatile protocol for the efficient synthesis of 3-aryl-2,3-dihydrobenzofuran (ADB) has been reported first. This reaction features the cyclization and aryl migration reaction of ortho-hydroxystilbene in ethanol, which is mediated by an iodonium ion, under ambient conditions. A class of ADB was prepared efficiently in good to excellent yields. Mechanism investigation revealed that acids and alcohols facilitated aryl migration, but alkaline and non-alcohol solvents promoted ß elimination. The practicality of this strategy was further substantiated by two scale-up reactions and demonstrated in efficient synthetic elaboration.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Tipo de estudo:
Guideline
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2023
Tipo de documento:
Article