Gold‐Catalyzed Dehydrogenative Cycloisomerization of 1,4‐Enyne Esters to 3,5‐Disubstituted Phenol Derivatives

A method to prepare synthetically important 3,5‐disubstituted phenol derivatives that relies on the sequential gold(I)‐catalyzed dehydrogenative cycloisomerization of 1,4‐enyne esters in the presence of 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) or N‐fluorobenzenesulfonimide (NFSI) is described. The...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-12, Vol.359 (24), p.4359-4368
Main Authors: Chen, Cuili, Chen, Xianxiao, Zhang, Xiaoxiang, Wang, Shifa, Rao, Weidong, Chan, Philip Wai Hong
Format: Article
Language:English
Subjects:
1,4-enyne esters
3,5-disubstituted phenols
Chemical synthesis
Dehydrogenation
dehydrogenative cycloisomerization
Derivatives
Esters
Gold
homogeneous catalysis
Isomerization
Phenols
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Summary:A method to prepare synthetically important 3,5‐disubstituted phenol derivatives that relies on the sequential gold(I)‐catalyzed dehydrogenative cycloisomerization of 1,4‐enyne esters in the presence of 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) or N‐fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram‐scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701068