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Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides.
J Org Chem. 2022 12 16; 87(24):16343-16350.JO

Abstract

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.

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Authors+Show Affiliations

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.

MeSH

PalladiumAldehydesCatalysisMolecular StructureIodidesKetonesQuinolines

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

36413613

Citation

Thakur, Dinesh Gopichand, et al. "Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences Between Aryl (Pseudo) Halides." The Journal of Organic Chemistry, vol. 87, no. 24, 2022, pp. 16343-16350.
Thakur DG, Sahoo T, Sen C, et al. Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides. J Org Chem. 2022;87(24):16343-16350.
Thakur, D. G., Sahoo, T., Sen, C., Rathod, N., & Ghosh, S. C. (2022). Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides. The Journal of Organic Chemistry, 87(24), 16343-16350. https://doi.org/10.1021/acs.joc.2c02011
Thakur DG, et al. Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences Between Aryl (Pseudo) Halides. J Org Chem. 2022 12 16;87(24):16343-16350. PubMed PMID: 36413613.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides. AU - Thakur,Dinesh Gopichand, AU - Sahoo,Tapan, AU - Sen,Chiranjit, AU - Rathod,Nilesh, AU - Ghosh,Subhash Chandra, Y1 - 2022/11/22/ PY - 2022/11/23/pubmed PY - 2022/12/20/medline PY - 2022/11/22/entrez SP - 16343 EP - 16350 JF - The Journal of organic chemistry JO - J Org Chem VL - 87 IS - 24 N2 - 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/36413613/Palladium_Catalyzed_Directed_Aldehyde_C_H_Arylation_of_Quinoline_8_carbaldehydes:_Exploring_the_Reactivity_Differences_between_Aryl__Pseudo__Halides_ DB - PRIME DP - Unbound Medicine ER -