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Chemoselective Palladium‐Catalyzed Direct C–H Arylation of 5‐Carboxyimidazoles: Unparalleled Access to Fused Imidazole‐Based Tricycles Containing Six‐, Seven‐ or Eight‐Membered Rings
Author(s) -
Thireau Jérémy,
Schneider Cédric,
Baudequin Christine,
Gaurrand Sandrine,
Angibaud Patrick,
Meerpoel Lieven,
Levacher Vincent,
Querolle Olivier,
Hoarau Christophe
Publication year - 2017
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.201700297
Subject(s) - chemistry , imidazole , palladium , intramolecular force , catalysis , halide , combinatorial chemistry , chemoselectivity , ring (chemistry) , solvent , stereochemistry , organic chemistry
An extensive study of the chemoselective Pd‐catalyzed inter‐ and intramolecular direct C–H arylation of N ‐benzylated 5‐carboxyimidazoles with halides with and without Cu I assistance in 1,4‐dioxane as a low‐polarity solvent was explored. The method was suitable for the synthesis of fused imidazole‐based tricyclic systems incorporating medium‐sized rings, including, for the first time, eight‐membered rings, which are valuable in modern drug design.