Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage

Mamoru Tobisu*, Tsuyoshi Takahira and Naoto Chatani*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: tobisuchem.eng.osaka-u.ac.jp, chatanichem.eng.osaka-u.ac.jp

M. Tobisu, T. Takahira, N. Chatani, Org. Lett., 2015, 17, 4352-4355.

DOI: 10.1021/acs.orglett.5b02200

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Abstract

The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand enables a nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents via cleavage of the C(aryl)-OMe bond. Various alkyl groups, including Me, Me₃SiCH₂, ArCH₂, adamantyl, and cyclopropyl can be introduced.

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1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents

M. Tobisu, A. Yasutome, H. Kinuta, K. Nakamura, N. Chatani, Org. Lett., 2014, 16, 5572-5575.

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Key Words

diarylmethanes

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ID: J54-Y2015