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Synfacts 2010(9): 1051-1051
DOI: 10.1055/s-0030-1257897
DOI: 10.1055/s-0030-1257897
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Nickel-Catalyzed Cross-Coupling of Aryl Grignard Reagents to Phenolate Salts
Contributor(s):Paul Knochel, Andreas J. WagnerD.-G. Yu, B.-J. Li, S.-F. Zheng, B.-T. Guan, B.-Q. Wang, Z.-J. Shi*
Peking University, Beijing, State Key Laboratory of Organometallic Chemistry, Shanghai and Sichuan Normal University, Chengdu, P. R. of China
Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents
Angew. Chem. Int. Ed. 2010, 49: 4566-4570
Peking University, Beijing, State Key Laboratory of Organometallic Chemistry, Shanghai and Sichuan Normal University, Chengdu, P. R. of China
Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents
Angew. Chem. Int. Ed. 2010, 49: 4566-4570
Further Information
Publication History
Publication Date:
23 August 2010 (online)
Key words
cross-coupling - aryl Grignard reagents - nickel
Significance
The first successful cross-coupling of 2-naphthol metal salts with various aryl Grignard reagents has been demonstrated. The process is atom-economical and gives a convenient access to various naphthalene derivatives.
Comment
It is important to note that the halide substituent on the Grignard reagent is critical to the reaction and a bromide was found to be the best. The most efficient solvent system is a mixture of toluene and diisopropyl ether (3:1), most likely because these solvents retain the metallic core framework due to their low coordinating ability.