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Synfacts 2015; 11(1): 0082
DOI: 10.1055/s-0034-1379657
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Tobsiu M, * Yasutome A, Kinuta H, Nakamura K, Chatani N. * Osaka University, Japan
1,3-Dicyclohexylimidazole-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Coupling of Aryl and Benzyl Methyl Ethers with Organoboron Reagents.

Org. Lett. 2014;
16: 5572-5575
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

nickel - Suzuki–Miyaura cross-coupling

Significance

The authors developed a novel nickel-based catalyst for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. The use of Ni(cod)2 and 1,3-dicyclohexylimidazol-2-ylidene (A) gave the expected products in good yields while showing good functional group tolerance.


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Comment

Notably, when using A instead of Cy3P, heteroaryl ethers were coupled in good yields (up to 96%), while the same reaction with Cy3P led to no product.


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