Copper-Catalyzed Difluoromethylation of Alkyl Iodides Enabled by Aryl Radical Activation of Carbon-Iodine Bonds was written by Cai, Aijie;Yan, Wenhao;Wang, Chao;Liu, Wei. And the article was included in Angewandte Chemie, International Edition in 2021.COA of Formula: C24H23ClO2 This article mentions the following:
A novel strategy that leveraged the halogen abstraction ability of aryl radicals, thereby engaging a diverse range of alkyl iodides in copper-catalyzed Negishi-type cross-coupling reactions at room temperature Specifically, aryl radicals generated via copper catalysis efficiently initiate the cleavage of the carbon-iodide bonds of alkyl iodides. The alkyl radicals thus generated enter the copper catalytic cycles to couple with a difluoromethyl zinc reagent, thus furnished the alkyl difluoromethane products. This unprecedented Negishi-type difluoromethylation approach was applied to the late-stage modification of densely functionalized pharmaceutical agents and natural products. In the experiment, the researchers used many compounds, for example, (Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7COA of Formula: C24H23ClO2).
(Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.COA of Formula: C24H23ClO2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts