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Palladium‐Catalyzed Synthesis of 2‐Aminoindoles by a Heteroanulation Reaction
Author(s) -
Witulski Bernhard,
Alayrac Carole,
TevzadzeSaeftel Lali
Publication year - 2003
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.200351977
Subject(s) - palladium , indole test , catalysis , chemistry , alkyne , amine gas treating , ring (chemistry) , nucleophile , chelation , combinatorial chemistry , coupling reaction , polymer chemistry , medicinal chemistry , organic chemistry
Chelates are the key : A conceptually novel indole ring forming reaction through heteroanulation is available through the palladium‐catalyzed reaction of N ‐alkenylanilides with primary or secondary amines. The key feature is the formation of an unprecedented σ ,π‐chelated palladium species (see scheme); nitrogen nucleophiles can add to the activated alkyne unit of this species to form the indole skeleton. (X=I, Br; HNR 2 R 3 =prim. or sec. amine; Ts=tosyl.)