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Direct Synthesis of alpha-Trifluoromethyl Ketone from (Hetero)arylacetylene: Design, Intermediate Trapping, and Mechanistic Investigations

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Title Direct Synthesis of alpha-Trifluoromethyl Ketone from (Hetero)arylacetylene: Design, Intermediate Trapping, and Mechanistic Investigations
 
Creator MAJI, A
HAZRA, A
MAITI, D
 
Subject SILYL ENOL ETHERS
COPPER-MEDIATED TRIFLUOROMETHYLATION
LIGHT PHOTOREDOX CATALYSIS
RADICAL TRIFLUOROMETHYLATION
MEDICINAL CHEMISTRY
CARBONYL-COMPOUNDS
ENANTIOSELECTIVE TRIFLUOROMETHYLATION
3-COMPONENT OXYTRIFLUOROMETHYLATION
CF3-TRANSFER REAGENTS
UNACTIVATED OLEFINS
 
Description Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O-2 to access medicinally active alpha-trifluoromethyl ketone compounds. This method was successful in producing alpha-trifluoromethyl ketone in heterocyclic scaffolds, which are incompatible with earlier strategies. Experimental findings suggest a mechanism involving alpha-styrenyl radical intermediate and 1-methyl-2-pyrroliclinone (NMP) solvent, which leads to crystallographically characterized N-methylsuccinimide. Isotope labeling, kinetic studies, and intermediate trapping further helped to gain insight into this energy-demanding process.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-28T12:53:58Z
2014-12-28T12:53:58Z
2014
 
Type Article
 
Identifier ORGANIC LETTERS, 16(17)4524-4527
1523-7060
1523-7052
http://dx.doi.org/10.1021/ol502071g
http://dspace.library.iitb.ac.in/jspui/handle/100/16618
 
Language English