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: sn17
st-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)
see article for more examples
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.
see article for more examples
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.
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
