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

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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol202248x

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

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.",

author = "Masahito Ochiai and Akira Yoshimura and Hoque, {Md Mahbubul} and Takuji Okubo and Motomichi Saito and Kazunori Miyamoto",

year = "2011",

month = oct,

day = "21",

doi = "10.1021/ol202248x",

language = "English",

volume = "13",

pages = "5568--5571",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane

AU - Ochiai, Masahito

AU - Yoshimura, Akira

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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U2 - 10.1021/ol202248x

DO - 10.1021/ol202248x

M3 - Article

C2 - 21919473

AN - SCOPUS:80054690764

VL - 13

SP - 5568

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

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

Abstract

ASJC Scopus subject areas

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