Nickel-Catalyzed Negishi Cross-Coupling Reactions of Secondary Alkylzinc Halides and Aryl Iodides

Amruta Joshi-Pangu, Madhu Ganesh and Mark R. Biscoe*

*Department of Chemistry, The City College of New York, 160 Convent Avenue, New York, New York 10031, United States, Email: mbiscoeccny.cuny.edu

A. Joshi-Pangu, M. Ganesh, M. R. Biscoe, Org. Lett., 2011, 13, 1218-1221.

DOI: 10.1021/ol200098d

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Abstract

A general Ni-catalyzed process for the cross-coupling of secondary alkylzinc halides and aryl/heteroaryl iodides overcomes the isomerization and β-hydride elimination problems that are associated with the use of secondary nucleophiles, and that have limited the analogous Pd-catalyzed systems. The presence of LiBF₄ dramatically improves both isomeric retention and yield for challenging substrates.

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Key Words

Negishi Coupling, Arenes

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ID: J54-Y2011-0600