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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

Mamoru Tobisu*, Ayaka Yasutome, Hirotaka Kinuta, Keisuke Nakamura and Naoto Chatani*

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

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

DOI: 10.1021/ol502583h (free Supporting Information)


Abstract

The use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene enables a cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.

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

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


Key Words

diarylmethanes, biaryls


ID: J54-Y2014