The site-selective dearomatization of naphthols is realized in astraightforward manner through a gold(I)- catalyzed [3,3]-sigmatropic rearrangement/allene function- alizationcascade sequence. The methodemploys readily available naph thylpropargyl ethers as startingmaterials. A range of denselyfunctionalized dihydrofurylnaphthalen-2(1H)-ones are obtained in high yields (up to 98 %) and extremely mild reactionconditions (reagent grade solvent, air,10 minute reaction time). Acomplete theoretical eluci- dation of the reaction machinery is also proposed, providing arationalefor important issues such as regio- and chemoselectivity.
Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes / Juzeng, An; Adriano, Parodi; Magda, Monari; Marta Castineira Reis, ; Carlos Silva Lopez, ; Marco, Bandini. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - ELETTRONICO. - 23:(2017), pp. 17473-17477. [10.1002/chem.201704942]
Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes
AN, JUZENG;Magda Monari;Marco Bandini
2017
Abstract
The site-selective dearomatization of naphthols is realized in astraightforward manner through a gold(I)- catalyzed [3,3]-sigmatropic rearrangement/allene function- alizationcascade sequence. The methodemploys readily available naph thylpropargyl ethers as startingmaterials. A range of denselyfunctionalized dihydrofurylnaphthalen-2(1H)-ones are obtained in high yields (up to 98 %) and extremely mild reactionconditions (reagent grade solvent, air,10 minute reaction time). Acomplete theoretical eluci- dation of the reaction machinery is also proposed, providing arationalefor important issues such as regio- and chemoselectivity.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
