Palladium-catalyzed direct C5-arylation or C4,C5-diarylation of 2-alkylisothiazol-3-ones
In: ISSN: 0040-4020 ; Tetrahedron ; https://univ-rennes.hal.science/hal-03735535 ; Tetrahedron, 2022, pp.132894. ⟨10.1016/j.tet.2022.132894⟩, 2022
Online
academicJournal
Zugriff:
International audience ; 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.
Titel: |
Palladium-catalyzed direct C5-arylation or C4,C5-diarylation of 2-alkylisothiazol-3-ones
|
---|---|
Autor/in / Beteiligte Person: | Mhadhbi, Oumaima ; Liu, Linhao ; Benzai, Amal ; Mellah, Besma ; Besbes, Néji ; Ollivier, Jerome ; Cordier, Marie ; Doucet, Henri ; Université de Tunis El Manar (UTM) ; Centre of Biotechnology Bordj Cedria ; Institut des Sciences Chimiques de Rennes (ISCR) ; Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes) ; Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS) ; We are grateful to the Scientific Ministry of Higher Education and Research of Tunisia for providing financial support to O. M. |
Link: | |
Zeitschrift: | ISSN: 0040-4020 ; Tetrahedron ; https://univ-rennes.hal.science/hal-03735535 ; Tetrahedron, 2022, pp.132894. ⟨10.1016/j.tet.2022.132894⟩, 2022 |
Veröffentlichung: | HAL CCSD ; Elsevier, 2022 |
Medientyp: | academicJournal |
DOI: | 10.1016/j.tet.2022.132894 |
Schlagwort: |
|
Sonstiges: |
|