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CH bond functionalization of aromatic heterocycles with chelating dicarbene palladium(II) and platinum(II) complexes
Author(s) -
Buscemi Gabriella,
Biffis Andrea,
Tubaro Cristina,
Basato Marino,
Graiff Claudia,
Tiripicchio Antonio
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1595
Subject(s) - chemistry , palladium , steric effects , yield (engineering) , chelation , platinum , catalysis , adduct , alkyne , combinatorial chemistry , medicinal chemistry , pincer movement , surface modification , halide , polymer chemistry , organic chemistry , materials science , metallurgy
Chelating dicarbene complexes of palladium(II) and platinum(II) catalyse at room temperature with 1% catalyst loading the reaction of ethyl phenylpropiolate with aromatic heterocycles to yield synthetically useful intermediates for fine chemicals without the need to use prefunctionalized substrates. The reaction outcome was found to be strongly dependent on the nature of the anionic ligands at the metal complex. Addition of silver salts to replace halide ligands with more weakly coordinating anions improves the reaction yield and changes the product distributions: heterocyclealkyne 2:1 adducts are obtained together with the usual hydroarylation products, which potentially broadens the scope of the reaction. The nature of the employed heterocycle, in particular its steric characteristics, is also found to strongly influence the outcome of the reaction. Copyright © 2009 John Wiley & Sons, Ltd.