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Palladium‐Catalyzed Cross‐Coupling of 1‐Aminoazoles with Aryl Chlorides: Application to the Synthesis of Unsymmetrical N,N′ ‐Diaryl‐1‐aminoindoles
Author(s) -
Brachet Etienne,
Messaoudi Samir,
Peyrat JeanFrançois,
Brion JeanDaniel,
Alami Mouad
Publication year - 2012
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.201200440
Subject(s) - chemistry , aryl , palladium , catalysis , combinatorial chemistry , coupling reaction , medicinal chemistry , organic chemistry , alkyl
An efficient method for the selective mono‐N‐arylation of 1‐aminoazoles to provide a range of N ‐aryl‐1‐aminoazoles in good yields is described. This process based on the use of tris(dibenzylideneacetone)dipalladium associated to Xphos as the catalyst system is general, and allows the coupling to proceed, for the first time, with a variety of cheaper and less reactive aryl chlorides. The sequential combination of selective monoarylation using aryl chlorides and a second N‐arylation reaction using (hetero)aryl bromides and iodides proved to be useful for the rapid construction of non‐symmetrical N , N′ ‐diaryl‐1‐aminoindoles in good yields.