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Palladium‐Catalyzed CS Activation/Aryne Insertion/Coupling Sequence: Synthesis of Functionalized 2‐Quinolinones
Author(s) -
Dong Ying,
Liu Bangyu,
Chen Peng,
Liu Qun,
Wang Mang
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310340
Subject(s) - aryne , intramolecular force , palladium , chemistry , nucleophile , ketene , catalysis , combinatorial chemistry , sequence (biology) , medicinal chemistry , stereochemistry , organic chemistry , biochemistry
The insertion of an aryne into a CS bond can suppress the addition of an S nucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc) 2 , a wide range of α‐carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2‐quinolinones in high yields under neutral reaction conditions by a CS activation/aryne insertion/intramolecular coupling sequence. The attractive feature of the new strategy also lies in the versatile transformations of the alkythio‐substituted quinolinone products.