Gold‐Catalyzed Dearomatization of 2‐Naphthols with Alkynes | Zendy

An Juzeng | Zendy; Parodi Adriano | Zendy; Monari Magda | Zendy; Reis Marta Castiñeira | Zendy; Lopez Carlos Silva | Zendy; Bandini Marco | Zendy

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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.

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