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Mechanistic Insights into Copper‐Catalyzed Sonogashira–Hagihara‐Type Cross‐Coupling Reactions: Sub‐Mol % Catalyst Loadings and Ligand Effects
Author(s) -
Zou LiangHua,
Johansson Adam Johannes,
Zuidema Erik,
Bolm Carsten
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300480
Subject(s) - sonogashira coupling , catalysis , copper , ligand (biochemistry) , chemistry , coupling reaction , kinetic energy , coupling (piping) , combinatorial chemistry , computational chemistry , materials science , palladium , organic chemistry , metallurgy , physics , biochemistry , receptor , quantum mechanics
An efficient catalytic system for Sonogashira–Hagihara‐type reactions displaying ligand acceleration in the copper‐catalyzed formation of C(sp 2 )C(sp) bonds is described. The structure of the ligand plays a key role for the coupling efficiency. Various copper sources show excellent catalytic activity, even in sub‐mol % quantities. A wide variety of substituents is tolerated in the substrates. Mechanistic details have been revealed by kinetic measurements and DFT calculations.