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Gold‐Catalyzed Dearomatization of 2‐Naphthols with Alkynes
Author(s) -
An Juzeng,
Parodi Adriano,
Monari Magda,
Reis Marta Castiñeira,
Lopez Carlos Silva,
Bandini Marco
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704942
Subject(s) - chemoselectivity , allene , reagent , catalysis , chemistry , combinatorial chemistry , solvent , reaction conditions , sequence (biology) , organic chemistry , biochemistry
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 H )‐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.