Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.
Cacchi, S., Fabrizi, G., Iazzetti, A., Molinaro, C., Verdiglione, R., Goggiamani, A., Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu, <<ADVANCED SYNTHESIS & CATALYSIS>>, 2015; 357 (5): 1053-1059. [doi:10.1002/adsc.201400881] [http://hdl.handle.net/10807/200525]
Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu
Iazzetti, Antonia;
2015
Abstract
Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.
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