Oxidation of fluoroalkyl alcohols using sodium hypochlorite pentahydrate [1]

• Published in: Journal of fluorine chemistry Vol. 243; pp. 109719 - 109728
• Main Authors: Kirihara, Masayuki, Suzuki, Katsuya, Nakakura, Kana, Saito, Katsuya, Nakamura, Riho, Tujimoto, Kazuki, Sakamoto, Yugo, Kikkawa, You, Shimazu, Hideo, Kimura, Yoshikazu
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.03.2021; Elsevier; Elsevier BV
• Subjects: Acetonitrile; Alcohol; Alcohols; Carbonyl compounds; Carbonyls; Catalysts; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Fluoroalkyl alcohol; Fluoroalkyl allylic alcohol; Fluoroalkyl α,β-epoxyketone hydrates; Hydrates; Oxidation; Physical Sciences; Science & Technology; Sodium; Sodium hypochlorite; Sodium hypochlorite pentahydrate; TEMPO; Fluoroalkyl α,β-epoxyketone hydrates; Fluoroalkyl allylic alcohol; Oxidation; TEMPO; Sodium hypochlorite pentahydrate; Fluoroalkyl alcohol; Fluoroalkyl alpha,beta-epoxyketone hydrates; EFFICIENT SYNTHESIS; NAOCL-CENTER-DOT-5HO CRYSTALS; DIFLUOROMETHYLATION; CATALYTIC-OXIDATION; OXIDANT; CHLORIDES; ARYL; TRIFLUOROMETHYL KETONES; CARBINOLS
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2020.109719

[Display omitted] •Fluoroalkyl alcohols are oxidized to the carbonyls by sodium hypochlorite pentahydrate in the presence of acid and TEMP catalyst.•Secondary fluoroalkyl alcohols are oxidized to the ketones by r sodium hypochlorite pentahydrate in the presence of acid without TEMPO.•Fluoroalkyl allylic alcohols reacted with sodium hypochlorite pentahydrate to produce the α,β-epoxyketone hydrates in high yields. Fluoroalkyl alcohols are effectivity oxidized to the corresponding fluoroalkyl carbonyl compounds by reaction with sodium hypochlorite pentahydrate in acetonitrile in the presence of acid and nitroxyl radical catalysts. Although the reaction proceeded slower under a nitroxyl radical catalyst- free condition, the desired carbonyl compounds were obtained in high yields. For the reaction with fluoroalkyl allylic alcohols, the corresponding α,β-epoxyketone hydrates were obtained in high yields.