Theoretical Study of the Reactivity of Phenyl Radicals Toward Enol Acetates

Carneiro, Leonardo S. A.; Real, Leticia H. S. P. C.; Buarque, Camilla D.; Esteves, Pierre M.

doi:10.21577/0103-5053.20200192

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“…This observation is similar to Konig's arylation process, 18 which indicates that diazonium salts with electron-withdrawing substituents are easier to be reduced to generate the corresponding aryl radicals because of having lower reduction potentials compared to diazonium salts with electron-donating substituents; thus, arylation with diazonium salts proceeds via aryl radical pathway. 18,19 Based on literature reports and experimental outcomes, a possible reaction mechanism is outlined in Scheme 3 for both reactions. First, the Pd(OAc) 2 and arylation are presented here, and efforts to expand the scope of this reaction are currently ongoing in our laboratory.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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

et al. 2022

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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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Section: ■ Results and Discussionmentioning

confidence: 99%