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Published August 10, 2009 | Supplemental Material
Journal Article Open

Competitive Benzene C−H Bond Activation versus Olefin Insertion in a (Monomethyl)palladium(II) β-Diketiminate Complex


The monomethylpalladium(II) complex (COD)Pd(CH_3)Cl (COD = 1,5-cyclooctadiene) is found to undergo both benzene C−H activation and migratory insertion of olefin, with the former faster than the latter, at room temperature in the presence of an anionic β-diketiminate ligand, to yield η^3-(6-R-cyclooctenyl)palladium(II) β-diketiminate (R = methyl or phenyl). The reaction is proposed to take place via the formation of a (monomethyl)palladium(II) β-diketiminate with COD as the fourth ligand, followed by competitive benzene C−H activation and migratory insertion of olefin. The proposed mechanism is supported by density functional theory calculations upon a simplified model system.

Additional Information

© 2009 American Chemical Society. Received March 3, 2009. Publication Date (Web): July 10, 2009. We thank Dr. Michael W. Day and Lawrence M. Henling for performing the X-ray crystallographic analysis. B.-L.L. also thanks George S. Chen for suggestions in preparing the manuscript. This work has been generously supported by BP through the MC2 program. Supporting Information: Detailed experimental and computational data. This material is available free of charge via the Internet at http://pubs.acs.org.

Attached Files

Supplemental Material - om900171d_si_001.pdf

Supplemental Material - om900171d_si_002.cif


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