Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane

Masahito Ochiai, Akira Yoshimura, Md Mahbubul Hoque, Takuji Okubo, Motomichi Saito, Kazunori Miyamoto

Research output: Contribution to journal › Article

17 Citations (Scopus)

Abstract

Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-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 intermediates will result in these differences in the reaction courses.

Original languageEnglish
Pages (from-to)5568-5571
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
Publication statusPublished - 21 Oct 2011
Externally publishedYes

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aldehydes
Aldehydes
aptitude
Oxidation
oxidation
Ethers
Methylene Chloride
Chloroform
chloroform
Fluorides
fluorides
ethers
oxygen atoms
Carbon
Electrons
Oxygen
Atoms
acids
Temperature
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. / Ochiai, Masahito; Yoshimura, Akira; Hoque, Md Mahbubul; Okubo, Takuji; Saito, Motomichi; Miyamoto, Kazunori.

In: Organic Letters, Vol. 13, No. 20, 21.10.2011, p. 5568-5571.

Research output: Contribution to journal › Article

Ochiai, M, Yoshimura, A, Hoque, MM, Okubo, T, Saito, M & Miyamoto, K 2011, 'Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane', Organic Letters, vol. 13, no. 20, pp. 5568-5571. https://doi.org/10.1021/ol202248x
Ochiai M, Yoshimura A, Hoque MM, Okubo T, Saito M, Miyamoto K. Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. Organic Letters. 2011 Oct 21;13(20):5568-5571. https://doi.org/10.1021/ol202248x
Ochiai, Masahito ; Yoshimura, Akira ; Hoque, Md Mahbubul ; Okubo, Takuji ; Saito, Motomichi ; Miyamoto, Kazunori. / Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. In: Organic Letters. 2011 ; Vol. 13, No. 20. pp. 5568-5571.
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AU - Saito, Motomichi

AU - Miyamoto, Kazunori

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AB - Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-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 intermediates will result in these differences in the reaction courses.

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