Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings

A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O...

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Published in:European journal of organic chemistry 2015-12, Vol.2015 (34), p.7475-7483
Main Authors: Moegling, Julian, Benischke, Andreas D., Hammann, Jeffrey M., Vepřek, Nynke A., Zoller, Florian, Rendenbach, Bettina, Hoffmann, Alexander, Sievers, Holger, Schuster, Michael, Knochel, Paul, Herres-Pawlis, Sonja
Format: Article
Language:English
Subjects:
Alkynes
C-C coupling
Copper
Cross-coupling
Homogeneous catalysis
N ligands
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Summary:A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O (10 mol‐%) under aerobic conditions and the corresponding chelate ligand (10 mol‐%), with its tailored facial coordination mode, is crucial for the success of the reaction. The coupling can also be carried out in water with liquid aryl halides and a phase‐transfer catalyst. A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of various iodoarenes with terminal alkynes. The reactions proceed under aerobic conditions, which makes this system synthetically highly useful. For liquid electrophiles, a substitution of DMF with water is possible when a phase‐transfer catalyst is provided.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501117