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

Pawaret Leowanawat, Na Zhang, Ana-Maria Resmerita, Brad M. Rosen and Virgil Percec*

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

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

DOI: 10.1021/jo202037x

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Abstract

Ni(COD)₂/PCy₃ is a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in THF at room temperature. This Ni-catalyzed cross-coupling tolerates electrophilic functionalities sensitive to organolithium and organomagnesium compounds.

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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

Suzuki Coupling, Biaryls

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ID: J42-Y2011-3520