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Gold‐Catalyzed Dehydrogenative Cycloisomerization of 1,4‐Enyne Esters to 3,5‐Disubstituted Phenol Derivatives
Author(s) -
Chen Cuili,
Chen Xianxiao,
Zhang Xiaoxiang,
Wang Shifa,
Rao Weidong,
Chan Philip Wai Hong
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701068
Subject(s) - cycloisomerization , chemistry , enyne , catalysis , phenol , combinatorial chemistry , adduct , organic chemistry
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.