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Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand

Chun Song, Yudao Ma, Qiang Chai, Chanqin Ma, Wei Jiang and Merritt B. Andrus*

*Brigham Young University, Department of Chemistry and Biochemistry, C100 BNSN, Provo, UT 84602, USA, Email: mbandruschem.byu.edu

C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron, 2005, 61, 7438-7446.

DOI: 10.1016/j.tet.2005.05.071



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Abstract

A novel bis-phenanthryl N-heterocyclic carbene (NHC) based palladium acetate catalyst was effective for the coupling of various aryl and vinyl chlorides with organoboron compounds. Hindered tri- and tetra-ortho substituted products were efficiently produced. Benzyl chloride was also found to be a useful coupling partner and trimethylboroxine was used to give methylated products.

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Key Words

Suzuki coupling, Imidazolium, Carbene, Palladium, Biaryls, Styrenes, Diarylmethanes, Methylation


ID: J72-Y2005-3000