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

Oscar Navarro, Harneet Kaur, Parisa Mahjoor and Steven P. Nolan*

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

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

DOI: 10.1021/jo035834p

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Abstract

Air- and moisture-stable (NHC)Pd(allyl)Cl complexes have been used in Suzuki-Miyaura cross-coupling, catalytic dehalogenation of aryl halides, and aryl amination. A general system involving (IPr)Pd(allyl)Cl as catalyst and NaO^tBu as base has proven to be highly active for all reactions. Microwave-assisted processes have afforded yields similar to those of the conventionally heated analogous reactions.

see article for more examples

see article for more examples

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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.

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

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

General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene System

J. Huang, G. Grasa, S. P. Nolan, Org. Lett., 1999, 1, 1307-1309.

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Key Words

Suzuki Coupling, Buchwald-Hartwig Coupling, Dehalogenations, Microwave Synthesis

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ID: J72-Y2004-480