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Convenient Synthesis of Alkenyl‐, Alkynyl‐, and Allenyl‐Substituted Imidazo[1,2‐ a ]pyridines via Palladium‐Catalyzed Cross‐Coupling Reactions
Author(s) -
EnguehardGueiffier Cécile,
Croix Cécile,
Hervet Maud,
Kazock JeanYves,
Gueiffier Alain,
Abarbri Mohamed
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790241
Subject(s) - chemistry , stille reaction , sonogashira coupling , palladium , substituent , pyridine , catalysis , combinatorial chemistry , simplicity , organic chemistry , medicinal chemistry , epistemology , philosophy
A systematic study on the Stille and Sonogashira cross‐coupling of iodinated imidazo[1,2‐ a ]pyridines was performed, permitting the preparation of various vinyl‐, ethynyl‐, and allenyl‐substituted derivatives. These methods are particularly valuable, given their experimental simplicity and high degree of flexibility with regard to functional groups that can be introduced in positions 3, 6, or 8 of the imidazo[1,2‐ a ]pyridine core. Effects concerning different substitution positions and the nature of the 2‐substituent under various reaction conditions are reported in detail for the above types of unsaturated groups introduced.