Pd-Catalyzed Direct C7 Trifluoromethylation of Indolines with Umemoto’s Reagent
An efficient palladium-catalyzed region-selective C7-trifluoromethylation of indolines using commercially available Umemoto’s reagent was reported. The reaction utilizing Umemoto’s reagent as CF3 radical precursor, pyrimidine as a removable directing group, Pd(II) as a catalyst, and Cu(II) as an o...
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| Veröffentlicht in: | Organic letters 2024-05, Vol.26 (18), p.3685-3690 |
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| container_title | Organic letters |
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| creator | Song, Qinglang Zhang, Lin Wang, Bin Chen, Ziren Jin, Weiwei Xia, Yu Wu, Shaofeng Liu, Chenjiang Zhang, Yonghong |
| description | An efficient palladium-catalyzed region-selective C7-trifluoromethylation of indolines using commercially available Umemoto’s reagent was reported. The reaction utilizing Umemoto’s reagent as CF3 radical precursor, pyrimidine as a removable directing group, Pd(II) as a catalyst, and Cu(II) as an oxidant furnished the required products with excellent regioselectivities and good yields. The present strategy has good region-selectivity, broad substrate scope, and scale-up application. Additionally, the present method was underlined by the direct C-1 trifluoromethylation of carbazoles. Furthermore, C7 trifluoromethylated indole can also be easily obtained via Pd-catalyzed direct C-7 trifluoromethylation/oxidation/deprotection sequential reactions. |
| doi_str_mv | 10.1021/acs.orglett.3c04123 |
| format | Article |
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The reaction utilizing Umemoto’s reagent as CF3 radical precursor, pyrimidine as a removable directing group, Pd(II) as a catalyst, and Cu(II) as an oxidant furnished the required products with excellent regioselectivities and good yields. The present strategy has good region-selectivity, broad substrate scope, and scale-up application. Additionally, the present method was underlined by the direct C-1 trifluoromethylation of carbazoles. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2024-05, Vol.26 (18), p.3685-3690 |
| issn | 1523-7060 1523-7052 1523-7052 |
| language | eng |
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| source | American Chemical Society Journals |
| subjects | carbazoles catalysts indoles oxidants oxidation |
| title | Pd-Catalyzed Direct C7 Trifluoromethylation of Indolines with Umemoto’s Reagent |
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