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Synthesis of Bis(heteroaryl) Ketones by Removal of Benzylic CHR and CO Groups

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Title Synthesis of Bis(heteroaryl) Ketones by Removal of Benzylic CHR and CO Groups
 
Creator MAJI, A
RANA, S
AKANKSHA
MAITI, D
 
Subject copper
heterocycles
ketones
oxygen
reaction mechanisms
CARBON BOND-CLEAVAGE
CATALYZED OXIDATIVE CLEAVAGE
BENZILIC ACID REARRANGEMENT
CROSS-COUPLING REACTION
MONO-ALPHA-ARYLATION
ARYL BORONIC ACIDS
ONE-POT SYNTHESIS
MOLECULAR-OXYGEN
TRIPLE BOND
EFFICIENT SYNTHESIS
 
Description A copper-catalyzed method for synthesis of diaryl ketones (Ar-CO-Ar') through removal of benzylic -CH2-, -CO-, and -CHR- groups from Ar-CO-CXR-Ar' has been discovered. A number of symmetrical and unsymmetrical heterocyclic ketones, which are usually difficult to synthesize, can be prepared in good to excellent yields. This method was applied to the synthesis of the nonsteroidal anti-inflammatory drug suprofen (47% yield over three steps). Based on preliminary mechanistic and kinetic studies, an active Cu/O-2 species is proposed to mediate the rearrangement reaction.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T12:46:55Z
2014-12-28T12:46:55Z
2014
 
Type Article
 
Identifier ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53(9)2428-2432
1433-7851
1521-3773
http://dx.doi.org/10.1002/anie.201308785
http://dspace.library.iitb.ac.in/jspui/handle/100/16593
 
Language English