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

Autor: Thakur DG; Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Sahoo T; Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Sen C; Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Rathod N; Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Ghosh SC; Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Dec 16; Vol. 87 (24), pp. 16343-16350. Date of Electronic Publication: 2022 Nov 22.
DOI: 10.1021/acs.joc.2c02011
Abstrakt: 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.
Databáze: MEDLINE
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