Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino Cyclization/Cycloisomerization.
J Org Chem
; 89(17): 12085-12093, 2024 Sep 06.
Article
in En
| MEDLINE
| ID: mdl-39180542
ABSTRACT
A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-ß-chloroenones is reported. This reaction proceeds via a syn-carbopalladation of the alkyne, followed by a vinyl-PdII-catalyzed cycloisomerization of the (E)-ß-chloroenone cascade, which provides an efficient method to synthesize furan-linked methylene oxindoles. The reaction features stereodefined vinyl-PdII species, high to excellent 5-exo/6-endo selectivity, excellent Z/E selectivity, and the sequential formation of three bonds and bis-heterocycles. The strategy for the synthesis of furan-containing benzofurans has also been demonstrated.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2024
Document type:
Article
Affiliation country:
China
Country of publication:
United States