Open AccessNickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C–O Bond Cleavage
Author(s) -
Mamoru Tobisu,
Tsuyoshi Takahira,
Naoto Chatani
Publication year - 2015
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.5b02200
Subject(s) - chemistry , alkyl , aryl , reagent , catalysis , bond cleavage , nickel , cleavage (geology) , ligand (biochemistry) , molecule , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , receptor , biochemistry , geotechnical engineering , fracture (geology) , engineering
Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)-OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules bearing a C(aryl)-OMe bond.