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Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N ‐Aryloxindole Nitrones
Author(s) -
Mo XueLing,
Chen ChunHua,
Liang Cui,
Mo DongLiang
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701324
Subject(s) - isatin , chemistry , nitrone , oxindole , yield (engineering) , catalysis , organic chemistry , acetylacetone , combinatorial chemistry , medicinal chemistry , cycloaddition , materials science , metallurgy
A variety of ( E )‐ N ‐aryloxindole nitrones were prepared in good to excellent yields by using a copper‐catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the ( E )‐oxindole nitrones. This method to prepare ( E )‐ N ‐aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone‐derived oxindole nitrone in high yield.