Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand |
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Authors: | Chun Song Qiang Chai Wei Jiang |
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Institution: | a Brigham Young University, Department of Chemistry and Biochemistry, C100 BNSN, Provo, UT 84602, USA b Chemistry College of Shandong University, Shanda South Road #27, Jinan, Shandong 250100, People's Republic of China c Shandong Academy of Medical Science, Jinan, Shandong 250062, People's Republic of China |
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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. N,N-Bis-(2,9-dicyclohexyl-10-phenanthryl)-4,5-dihydroimidazolium chloride 8 (H2ICP·HCl) with Pd(OAc)2 and KF·18-c-6 in THF at room temperature gave Suzuki-Miyaura coupling of aryl and vinyl chorides, including unactivated and di-ortho substituted substrates in high yields. Hindered tri- and tetra-ortho substituted products were also efficiently produced. Benzyl chloride was also found to be a useful coupling partner and trimethylboroxine was used to give methylated products. The effect of ligand, base, temperature, solvent, and reaction time are reported along with various substrates including halides and triflates. |
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Keywords: | Suzuki coupling Imidazolium Carbene Palladium |
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