Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes

作者：An Juzeng; Parodi Adriano; Monari Magda; Castineira Reis Marta; Silva Lopez Carlos; Bandini Marco

来源：Chemistry - A European Journal, 2017, 23(69): 17473-17477.

DOI：10.1002/chem.201704942

<jats:title>Abstract</jats:title><jats:p>The site‐selective dearomatization of naphthols is realized in a straightforward manner through a gold(I)‐catalyzed [3,3]‐sigmatropic rearrangement/allene functionalization cascade sequence. The method employs readily available naphthylpropargyl ethers as starting materials. A range of densely functionalized dihydrofurylnaphthalen‐2(1<jats:italic>H</jats:italic>)‐ones are obtained in high yields (up to 98 %) and extremely mild reaction conditions (reagent grade solvent, air, 10 minute reaction time). A complete theoretical elucidation of the reaction machinery is also proposed, providing a rationale for important issues such as regio‐ and chemoselectivity.</jats:p>

• 出版日期2017-12-11