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.
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/substitution reactions / Cacchi, Sandro; Fabrizi, Giancarlo; Iazzetti, Antonia; Molinaro, Carmela; Verdiglione, Rosanna; Goggiamani, Antonella. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:5(2015), pp. 1053-1059. [10.1002/adsc.201400881]
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/substitution reactions
CACCHI, Sandro;FABRIZI, Giancarlo;IAZZETTI, Antonia;MOLINARO, CARMELA;VERDIGLIONE, ROSANNA;GOGGIAMANI, ANTONELLA
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.File | Dimensione | Formato | |
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