Ortho-lithiation reaction of aryl triflones
| Autor: | Yuji Sumii, Xiu-Hua Xu, Norio Shibata, Misaki Taniguchi, Etsuko Tokunaga |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Steric effects Trifluoromethyl 010405 organic chemistry Metalation Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Coupling reaction 0104 chemical sciences Sulfone chemistry.chemical_compound chemistry Drug Discovery Moiety |
| Zdroj: | Tetrahedron. 74:5635-5641 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.07.055 |
| Popis: | The ortho-lithiation of substituted arenes is a powerful methodology to synthesize ortho-substituted arenes. While a wide variety of directed metalation groups (DMGs) have been reported, trifluoromethyl sulfone has never been used. We disclose the first example of ortho-lithiation of aryl triflones. We found that the trifluoromethyl sulfonyl group is not only an important structural motif in biologically active molecules and specialty materials, but also an excellent DMG moiety for ortho-metalation reactions. The use of a base that causes steric hindrance, LTMP, is the key for successful transformation to furnish a variety of ortho-substituted aryl triflones in good yields. Further functionalization of resulting ortho-substituted aryl triflones was demonstrated by metal-catalyzed coupling reactions. |
| Databáze: | OpenAIRE |
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