Zero-Valent Metals Accelerate the Neopentylglycolborylation of Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems

Pawaret Leowanawat, Ana-Maria Resmerita, Costel Moldoveanu, Chi Liu, Na Zhang, Daniela A. Wilson, Lisa M. Hoang, Brad M. Rosen and Virgil Percec*

*Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, Email: percecsas.upenn.edu

P. Leowanawat, A.-M. Resmerita, C. Moldoveanu, C. Liu, N. Zhang, D. A. Wilson, L. M. Hoang, B. M. Rosen, V. Persec, J. Org. Chem., 2010, 75, 7822-7828.

DOI: 10.1021/jo101718v

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Abstract

The highly active mixed-ligand catalytic system NiCl₂(dppp)/dppf combined with the reducing effect of zerovalent Zn enables a dramatic acceleration of the rate of the neopentylglycolborylation of aryl halides. A diversity of electron-rich and electron-deficient aryl iodides, bromides, and chlorides were efficiently neopentylglycolborylated in very good yields, typically in 1 h or less.

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Neopentylglycolborylation of Aryl Mesylates and Tosylates Catalyzed by Ni-Based Mixed-Ligand Systems Activated with Zn

D. A. Wilson, C. J. Wilson, C. Moldoveanu, A.-M. Resmerita, P. Corcoran, L. M. Hoang, B. M. Rosen, V. Percec, J. Am. Chem. Soc., 2010, 132, 1800-1801.

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Key Words

Aryl Boronates, Zinc

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ID: J42-Y2010-3190