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Divergent Reactivity in Palladium-Catalyzed Annulation with Diarylamines and ,-Unsaturated Acids: Direct Access to Substituted 2-Quinolinones and Indoles

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Title Divergent Reactivity in Palladium-Catalyzed Annulation with Diarylamines and ,-Unsaturated Acids: Direct Access to Substituted 2-Quinolinones and Indoles
 
Creator KANCHERLA, R
NAVEEN, T
MAITI, D
 
Subject H BOND ACTIVATION
FUJIWARA-MORITANI REACTION
C-H
AROMATIC-SUBSTITUTION
ROOM-TEMPERATURE
HECK REACTION
REDUCTIVE ANNULATION
SELECTIVE ARYLATION
EFFICIENT SYNTHESIS
COUPLING REACTIONS
amines
carboxylic acids
CH activation
indoles
palladium
 
Description A palladium-catalyzed CH activation strategy has been successfully employed for exclusive synthesis of a variety of 3-substituted indoles. A [3+3] annulation for synthesizing substituted 2-quinolinones was recently developed by reaction of ,-unsaturated carboxylic acids with diarylamines under acidic conditions. In the present work, an analogous [3+2] annulation is achieved from the same set of starting materials under basic conditions to generate 1,3-disubstituted indoles exclusively. Mechanistic studies revealed an ortho-palladation--coordination--migratory insertion--hydride elimination reaction sequence to be operative under the reaction conditions.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:30:08Z
2016-01-14T10:30:08Z
2015
 
Type Article
 
Identifier CHEMISTRY-A EUROPEAN JOURNAL, 21(24)8723-8726
0947-6539
1521-3765
http://dx.doi.org/10.1002/chem.201501208
http://dspace.library.iitb.ac.in/jspui/handle/100/17363
 
Language en