Palladium‐Catalyzed Domino Heck/Phosphorylation towards 3,3‐Disubstituted Phosphinonyloxindoles

The first Pd‐catalyzed domino Heck/phosphorylation of N‐(2‐iodophenyl)acrylamides with secondary phosphine oxides has been developed. The use of PdCl2 as a catalyst, 1,4‐bis(diphenylphosphino)butane as a ligand, K2CO3 as a base, various N‐(2‐iodophenyl)acrylamide derivatives are tolerant in this tra...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-11, Vol.361 (21), p.4961-4965
Main Authors: Lu, Guozhang, Huangfu, Xinlei, Wu, Zi'ang, Tang, Guo, Zhao, Yufen
Format: Article
Language:English
Subjects:
Acrylamide
Heck reaction
heterocycles
oxindoles
Palladium
phosphorus
Phosphorylation
Potassium carbonate
Transformations
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Summary:The first Pd‐catalyzed domino Heck/phosphorylation of N‐(2‐iodophenyl)acrylamides with secondary phosphine oxides has been developed. The use of PdCl2 as a catalyst, 1,4‐bis(diphenylphosphino)butane as a ligand, K2CO3 as a base, various N‐(2‐iodophenyl)acrylamide derivatives are tolerant in this transformation, affording 3‐phosphinomethyl 3,3‐disubstituted oxindole products in good to excellent yields. This transformation offers a straightforward route to the formation of the new C−C and P−C bonds, oxindole ring in one step. Moreover, this method can be easily adapted to large‐scale preparation.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901100