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

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 language	English
Pages (from-to)	5568-5571
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	20
DOIs	https://doi.org/10.1021/ol202248x
Publication status	Published - 21 Oct 2011
Externally published	Yes

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Ochiai, M., Yoshimura, A., Hoque, M. M., Okubo, T., Saito, M., & Miyamoto, K. (2011). Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ ³-bromane. Organic Letters, 13(20), 5568-5571. https://doi.org/10.1021/ol202248x

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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.",

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AU - Ochiai, Masahito

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AU - Hoque, Md Mahbubul

AU - Okubo, Takuji

AU - Saito, Motomichi

AU - Miyamoto, Kazunori

PY - 2011/10/21

Y1 - 2011/10/21

N2 - 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.

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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10.1021/ol202248x