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Sequential Metal‐Catalyzed N ‐Heteroarylation and C–C Cross‐Coupling Reactions: An Expedient Route to Tris(hetero)aryl Systems
Author(s) -
Siddle Jamie S.,
Batsanov Andrei S.,
Bryce Martin R.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800018
Subject(s) - chemistry , aryl , benzimidazole , reagent , tris , catalysis , palladium , imidazole , combinatorial chemistry , pyrrole , metal , coupling reaction , copper , medicinal chemistry , organic chemistry , biochemistry , alkyl
This paper describes copper‐catalyzed N–C heteroarylation of benzimidazole, 1‐methylbenzimidazolone, imidazole and pyrrole. The products of these reactions then undergo palladium‐catalyzed C–C cross‐couplings with aryl or heteroarylboronic acids under Suzuki–Miyaura conditions to provide a rapid entry, from readily‐available reagents, into tris(hetero)aryl scaffolds comprising two or three N‐heterocyclic rings. The sequential N–C and C–C couplings can be performed in a one‐pot process (two examples are given: >50 % overall yields). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)