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Nickel Carbodicarbene Catalyzes Kumada Cross‐Coupling of Aryl Ethers with Grignard Reagents through C–O Bond Activation
Author(s) -
Ambre Ram,
Yang Hsuan,
Chen WenChing,
Yap Glenn P. A.,
Jurca Titel,
Ong TiowGan
Publication year - 2019
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201900692
Subject(s) - chemistry , aryl , reagent , nickel , cleavage (geology) , combinatorial chemistry , bond cleavage , coupling reaction , catalysis , medicinal chemistry , grignard reagent , stereochemistry , organic chemistry , alkyl , geotechnical engineering , fracture (geology) , engineering
The development of a cross‐coupling reaction protocol between aryl ethers and Grignard reagents catalyzed by carbodicarbene (CDC) nickel complexes to afford biaryl compounds through C–O cleavage is reported. Aromatic substrates featuring a broad range of electron neutral, donating, or withdrawing groups are introduced at the desired position. The method has proven effective over a wide range of naphthyl methyl ethers, anisoles, and Grignard reagents. The robustness of the protocol is validated by performing multiple cleavage reactions, gram scale synthesis, and arylation of a dimethoxy esterdiol derivative.