Palladium-Catalyzed Directed Aldehyde C–H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides

Palladium-Catalyzed Directed Aldehyde C–H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides

We have developed a method for Pd-catalyzed direct C–H arylation of quinoline-8-carbaldehydes with either aryl iodides or aryl diazonium salts for the synthesis of aryl quinolinyl ketones. Aryl iodide substituted with an electron-donating group favors the reaction, whereas aryl diazonium salt substi...

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Veröffentlicht in:Journal of organic chemistry 2022-12, Vol.87 (24), p.16343-16350
Hauptverfasser: Thakur, Dinesh Gopichand, Sahoo, Tapan, Sen, Chiranjit, Rathod, Nilesh, Ghosh, Subhash Chandra
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Catalysis
Iodides
Ketones
Molecular Structure
Palladium
Quinolines
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container_end_page 16350
container_issue 24
container_start_page 16343
container_title Journal of organic chemistry
container_volume 87
creator Thakur, Dinesh Gopichand
Sahoo, Tapan
Sen, Chiranjit
Rathod, Nilesh
Ghosh, Subhash Chandra
description We have developed a method for Pd-catalyzed direct C–H arylation of quinoline-8-carbaldehydes with either aryl iodides or aryl diazonium salts for the synthesis of aryl quinolinyl ketones. Aryl iodide substituted with an electron-donating group favors the reaction, whereas aryl diazonium salt substituted with an electron-withdrawing group showed excellent reactivity. A range of aryl quinolinyl ketones were synthesized in good-to-excellent yields, with very good functional group tolerance. Our methodology was successfully applied to synthesize highly potent tubulin polymerization inhibitors and can be easily scaled up to a gram scale.
doi_str_mv 10.1021/acs.joc.2c02011
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subjects Aldehydes
Catalysis
Iodides
Ketones
Molecular Structure
Palladium
Quinolines
title Palladium-Catalyzed Directed Aldehyde C–H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides
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