Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro (aryl)-λ3-bromane

M Ochiai, A Yoshimura, MM Hoque, T Okubo…

文献索引：Ochiai, Masahito; Yoshimura, Akira; Hoque, Md. Mahbubul; Okubo, Takuji; Saito, Motomichi; Miyamoto, Kazunori Organic Letters, 2011 , vol. 13, # 20 p. 5568 - 5571

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被引用次数: 16

摘要

Oxidation of primary aliphatic aldehydes with p-trifluoromethylphenyl (difluoro)-λ3-bromane in dichloromethane at 0° C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1, 2- shift from carbon to an electron-deficient oxygen atom in bromane (III) Criegee-type ...