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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
Author(s) -
Cacchi Sandro,
Fabrizi Giancarlo,
Iazzetti Antonia,
Molinaro Carmela,
Verdiglione Rosanna,
Goggiamani Antonella
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400881
Subject(s) - sonogashira coupling , chemistry , palladium , copper , domino , cascade reaction , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry
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.