Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 24, Pages 4359-4368Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701068
Keywords
dehydrogenative cycloisomerization; 3,5-disubstituted phenols; 1,4-enyne esters; gold; homogeneous catalysis
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Funding
- National Natural Science Foundation of China [21502093, 21302096]
- Natural Science Foundation of Jiangsu Province [BK20150871, BK20171449]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
- Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP)
- Australian Research Council [DP160101682]
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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.
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