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

Daniela A. Wilson, Christopher J. Wilson, Costel Moldoveanu, Ana-Maria Resmerita, Patrick Corcoran, 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

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.

DOI: 10.1021/ja910808x

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Abstract

The mixed-ligand system NiCl₂(dppp)/dppf is an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electron-deficient aryl mesylates and tosylates. The addition of Zn powder as a reductant dramatically increases the reaction yield and reduces the reaction time, providing complete conversion in 1-3 h.

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

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.

Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature

P. Leowanawat, N. Zhang, A.-M. Remerita, B. M. Rosen, V. Percec, J. Org. Chem., 2011, 76, 9946-9955.

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Key Words

Aryl Boronates, Zinc

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ID: J48-Y2010-0490