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Direct Synthesis of 2‐(Aminomethyl)indoles through Copper(I)‐Catalyzed Domino Three‐Component Coupling and Cyclization Reactions
Author(s) -
Ohno Hiroaki,
Ohta Yusuke,
Oishi Shinya,
Fujii Nobutaka
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604342
Subject(s) - indole test , catalysis , chemistry , domino , copper , palladium , component (thermodynamics) , combinatorial chemistry , tying , surface modification , coupling (piping) , coupling reaction , stereochemistry , organic chemistry , materials science , computer science , physics , metallurgy , thermodynamics , operating system
Tying up loose ends : A copper(I)‐catalyzed three‐component reaction has been developed that leads to the formation of 2‐(aminomethyl)indole derivatives. Water is the sole theoretical by‐product in this reaction in which two CN bonds and one CC bond are formed. This route to the indole nucleus in combination with a palladium‐catalyzed functionalization of a CH bond is also useful for the synthesis of polycyclic indoles (see scheme).