Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation [electronic resource] : Expanded Scope Through Mechanistic Insight
- Berkeley, Calif. : Lawrence Berkeley National Laboratory, 2007.
Oak Ridge, Tenn. : Distributed by the Office of Scientific and Technical Information, U.S. Dept. of Energy.
- Additional Creators:
- Lawrence Berkeley National Laboratory
United States. Department of Energy. Office of Scientific and Technical Information
- A practical, functional group tolerant method for the Rh-catalyzed direct arylation of a variety of pharmaceutically important azoles with aryl bromides is described. Many of the successful azole and aryl bromide coupling partners are not compatible with methods for the direct arylation of heterocycles using Pd(0) or Cu(I) catalysts. The readily prepared, low molecular weight ligand, Z-1-tert-butyl-2,3,6,7-tetrahydrophosphepine, which coordinates to Rh in a bidentate P-olefin fashion to provide a highly active yet thermally stable arylation catalyst, is essential to the success of this method. By using the tetrafluoroborate salt of the corresponding phosphonium, the reactions can be assembled outside of a glove box without purification of reagents or solvent. The reactions are also conducted in THF or dioxane, which greatly simplifies product isolation relative to most other methods for direct arylation of azoles employing high-boiling amide solvents. The reactions are performed with heating in a microwave reactor to obtain excellent product yields in two hours.
- Published through SciTech Connect.
Journal of the American Chemical Society ISSN 0002-7863; JACSAT FT
Bergman, Robert; Ellman, Jonathan; Lewis, Jared; Berman, Ashley.
Chemical Sciences Division
- Funding Information:
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