Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino
Yujie Yi1, Ye Yuan2, Songsong Zhu3
1Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.
Abstract:
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.
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