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Palladium-catalyzed direct C5-arylation or C4,C5-diarylation of 2-alkylisothiazol-3-ones
| Content Provider | Hyper Articles en Ligne (HAL) |
|---|---|
| Author | Mhadhbi, Oumaima Liu, Linhao Benzai, Amal Mellah, Besma Besbes, Néji Ollivier, Jerome Cordier, Marie Doucet, Henri |
| Abstract | The regioselectivity of the Pd-catalyzed direct arylation of unsubstituted 2-alkylisothiazol-3(2H)-ones was investigated. Conditions for the regioselective palladium-catalyzed direct C5-arylation of 2-alkylisothiazol-3-ones using aryl bromides as the coupling partners are reported. This procedure tolerates a wide variety of substituents such as nitro, nitrile, ester, chloro, fluoro, trifluoromethyl, trifluoromethoxy, difluoromethoxy at para-, meta- and also ortho-positions on the aryl bromide. Both methyl- and octyl-substituents at 2-position of alkylisothiazol-3-ones are tolerated. Moreover, at a more elevated temperature in the presence of a larger excess of the aryl bromide, the access to the C4,C5-diarylated alkylisothiazol-3-ones is also possible, revealing that the C4-position of isothiazol-3(2H)-ones is reactive for direct arylation when the C5-position is blocked. Therefore, this method provides a one pot access to a wide variety of isothiazolinone derivatives allowing to modify easily their biological properties. |
| Related Links | https://univ-rennes.hal.science/hal-03735535/file/Oumaima%20Tet%20Hal.pdf |
| ISSN | 00404020 |
| DOI | 10.1016/j.tet.2022.132894 |
| Journal | Tetrahedron |
| Language | English |
| Publisher | HAL CCSD Elsevier |
| Publisher Date | 2022-08-13 |
| Access Restriction | Open |
| Subject Keyword | Palladium C–H bond functionalization Homogeneous catalysis Direct arylation isothiazolinones Chemical Sciences |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Drug Discovery Biochemistry Chemical Engineering |
