Synthesis 2021; 53(04): 775-784
DOI: 10.1055/s-0040-1707371
paper

From Furan–Yne Systems to para-Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate

Saman Ahmadi
,
Mohammad Ghanbari
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran   Email: ghanbari-m@kashanu.ac.ir
› Author Affiliations
University of Kashan (Grant Number 573600/3).


Abstract

A series of furan–yne systems were transformed into the corresponding para-benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para-benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes.

Supporting Information



Publication History

Received: 19 January 2020

Accepted after revision: 01 August 2020

Article published online:
23 September 2020

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