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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J. Huang, G. Grasa, S. P. Nolan, Org. Lett., 1999, 1, 1307-1309.
O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem., 2004, 69, 3173-3180.
N. Marion, E. C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, S. P. Nolan, J. Org. Chem., 2006, 71, 3816-3821.
Key Words
Suzuki Coupling, Buchwald-Hartwig Reaction
ID: J48-Y2006-1760