Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino Cyclization/Cycloisomerization

A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-β-chloroenones is reported. This reaction proceeds via a syn-carbopalladation of the alkyne, followed by a vinyl-PdII-catalyzed cycloisomerization of the (E)-β-chloroenone cascade, wh...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2024-09, Vol.89 (17), p.12085-12093
Main Authors: Yi, Yujie, Yuan, Ye, Zhu, Songsong, Wang, Jinbei, Wang, Zhaolin, Zhang, Jingli, Gao, Guanbin, Sun, Taolei
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-β-chloroenones is reported. This reaction proceeds via a syn-carbopalladation of the alkyne, followed by a vinyl-PdII-catalyzed cycloisomerization of the (E)-β-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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00895