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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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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cited_by cdi_FETCH-LOGICAL-c4608-97b27bae9d8a21ca53747fc507ff53565d835ebb8e4f13eb3bd53f963b930a903
cites cdi_FETCH-LOGICAL-c4608-97b27bae9d8a21ca53747fc507ff53565d835ebb8e4f13eb3bd53f963b930a903
container_end_page 4368
container_issue 24
container_start_page 4359
container_title Advanced synthesis & catalysis
container_volume 359
creator Chen, Cuili
Chen, Xianxiao
Zhang, Xiaoxiang
Wang, Shifa
Rao, Weidong
Chan, Philip Wai Hong
description 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.
doi_str_mv 10.1002/adsc.201701068
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subjects 1,4-enyne esters
3,5-disubstituted phenols
Chemical synthesis
Dehydrogenation
dehydrogenative cycloisomerization
Derivatives
Esters
Gold
homogeneous catalysis
Isomerization
Phenols
title Gold‐Catalyzed Dehydrogenative Cycloisomerization of 1,4‐Enyne Esters to 3,5‐Disubstituted Phenol Derivatives
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