| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1323385 | Journal of Organometallic Chemistry | 2015 | 7 Pages |
•Propargylic ethers instead of propargylic acetates can react in gold catalysis.•α-Naphthols can conveniently be obtained this way.•The new product type probably is generated by a new mechanistic pathway.
Diyne substrates bearing one propargylic ether instead of the previously published propargylic acetates were subjected to a gold catalyst. α−Naphthol derivatives were obtained as products of the cycloisomerization. The close relationship of the products to the corresponding cyclizations implicated a related mechanistic scenary at first, but further studies favour a mechanistic pathway that is completely different.
Graphical abstractDiynes with an alkoxy substitution in propargylic position deliver α-naphtholes via a cycloisomerization that is most probably initiated by a nucleophilic attack of the tert-butyl alkyne.Figure optionsDownload full-size imageDownload as PowerPoint slide
