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Rational Exploration of N-Heterocyclic Carbene (NHC) Palladacycle Diversity: A Highly Active and Versatile Precatalyst for Suzuki-Miyaura Coupling Reactions of Deactivated Aryl and Alkyl Substrates

Guang-Rong Peh, Eric Assen B. Kantchev*, Jun-Cheng Er, Jackie Y. Ying*

*Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Email:,

G.-R. Peh, E. A. B. Kantchev, J.-C. Er, J. Y. Ying, Chem. Eur. J., 2010, 14, 4010-4017.

DOI: 10.1002/chem.200902842


The evaluation of a small, rationally designed library of NHC-palladacycles showed, that combining the bulky N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) with cyclopalladated acetanilide as the optimal palladium precatalyst leads to superior catalytic activity in sp2-sp2, sp2-sp3 and sp3-sp3 Suzuki-Miyaura coupling reactions.

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Key Words

Suzuki Coupling, Biaryls, Alkyl-substituted Arenes

ID: JXX-Y2010-3620