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Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions

Nicolas Marion, Oscar Navarro, Jianguo Mei, Edwin D. Stevens, Natalie M. Scott and Steven P. Nolan*

*School of Chemistry, University of St Andrews, St Andrews KY16 9ST, U.K., Email: sn17st-andrews.ac.uk

N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc., 2006, 128, 4101-4111.

DOI: 10.1021/ja057704z (free Supporting Information)



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Abstract

When (NHC)Pd(R-allyl)Cl complexes are compared to (NHC)Pd(allyl)Cl, substitution at the terminal position of the allyl scaffold favors a more facile activation step and a higher catalytic activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions. In both reactions, extremely hindered substrates and aryl chlorides can be coupled at room temperature in minutes.

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Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic carbene)Pd(allyl)Cl Complexes

O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem., 2004, 69, 3173-3180.

(IPr)Pd(acac)Cl: An Easily Synthesized, Efficient, and Versatile Precatalyst for C-N and C-C Bond Formation

N. Marion, E. C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, S. P. Nolan, J. Org. Chem., 2006, 71, 3816-3821.

Rapid Room Temperature Buchwald-Hartwig and Suzuki-Miyaura Couplings of Heteroaromatic Employing Low Catalyst Loadings

O. Navarro, N. Marion, J. Mei, S.P. Nolan, Chem. Eur. J., 2006, 12, 5142-5148. DOI: 10.1002/chem.200600283


Key Words

Suzuki Coupling, Buchwald-Hartwig Reaction


ID: J48-Y2006-1760