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Palladium-Catalyzed Cyclization Coupling with Cyclobutanone-Derived N -Tosylhydrazones: Synthesis of Benzofuran-3-Cyclobutylidenes and Spirocyclobutanes.

Jie SunHao YeHaibin ZhangXin-Xing Wu
Published in: The Journal of organic chemistry (2023)
A palladium-catalyzed cyclization coupling of iodoarene-tethered alkynes with cyclobutanone-derived N -tosylhydrazones is reported, providing a convenient and efficient approach to benzofuran-3-cyclobutylidenes. On this basis, spirocyclobutanes can be generated smoothly in an efficient cascade manner by the addition of dienophiles. Good yields and scalability are demonstrated. Sequential intramolecular carbopalladation, palladium-carbene migratory insertion, δ-hydride elimination, and cycloaddition processes are involved.
Keyphrases
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