Palladacycle as highly efficient catalyst for ring opening of oxabicyclic alkenes with organozinc halides

Ring opening reaction of oxabicylic alkenes 4 with in situ prepared organozinc halides 5 was catalyzed by palladacycle 3 with high efficiency. Good yields of the corresponding 1,2-dihydronaphth-1-ols (6) were provided when as low as 0.05 mol% of palladacycle 3 was used. 31P NMR study showed that the skeleton of 3 remained intact in the reaction, which implied that palladacycle 3 did not serve as a catalyst precursor but a catalyst in the reaction.

Graphical abstractPalladacycle 3 is a highly active catalyst in ring opening reaction of oxabicylic alkenes 4 with in situ prepared organozinc halides 5. 31P NMR study showed that the skeleton of 3 remained intact in the reaction, which implied that palladacycle 3 might be a real catalyst in the reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide