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Título: | Rhodium-promoted C–H bond activation of quinoline, methylquinolines, and related mono-substituted quinolines |
Autor: | Heras, Laura A. de las CSIC; Esteruelas, Miguel A. CSIC ORCID; Oliván, Montserrat CSIC ORCID ; Oñate, Enrique CSIC ORCID | Fecha de publicación: | 2022 | Editor: | American Chemical Society | Citación: | Organometallics 41(16): 2317-2326 (2022) | Resumen: | The C–H bond activation of methylquinolines, quinoline, 3-methoxyquinoline, and 3-(trifluoromethyl)quinoline promoted by the square-planar rhodium(I) complex RhH{κ3-P,O,P-[xant(PiPr2)2]} [1; xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene] has been systematically studied. Results reveal that the activation of the heteroring is preferred over the activation of the carbocycle, and the activated position depends upon the position of the substituent in the substrate. Thus, 3-, 4-, and 5-methylquinoline reacts with 1 to quantitatively form square-planar rhodium(I)-(2-quinolinyl) derivatives, whereas 2-, 6-, and 7-methylquinoline quantitatively leads to rhodium(I)-(4-quinolinyl) species. By contrast, quinoline and 8-methylquinoline afford mixtures of the respective rhodium(I)-(2-quinolinyl) and -(4-quinolinyl) complexes. 3-Methoxyquinoline displays the same behavior as that of 3-methylquinoline, while 3-(trifluoromethyl)quinoline yields a mixture of rhodium(I)-(2-quinolinyl), -(4-quinolinyl), -(6-quinolinyl), and -(7-quinolinyl) isomers. | Versión del editor: | https://doi.org/10.1021/acs.organomet.2c00270 | URI: | http://hdl.handle.net/10261/278173 | DOI: | 10.1021/acs.organomet.2c00270 | E-ISSN: | 1520-6041 |
Aparece en las colecciones: | (ISQCH) Artículos |
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Laura-Organometallics2022-41-2317.pdf | 2,02 MB | Adobe PDF | Visualizar/Abrir |
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