AI Article Synopsis
- A new method using Rh catalysts allows for direct arylation of azoles with aryl bromides, overcoming limitations of traditional Pd and Cu methods.
- The combination of the unique ligand Z-1-tert-butyl-2,3,6,7-tetrahydrophosphepine and a convenient tetrafluoroborate salt enables reactions to be set up easily outside of a glovebox.
- Conducting these reactions in THF or dioxane and using microwave heating leads to high product yields in just 2 hours.
Article Abstract
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 glovebox 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 2 h.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2693036 | PMC |
| http://dx.doi.org/10.1021/ja0748985 | DOI Listing |
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