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 journalArticle

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

Fingerprint

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 journalArticle

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, 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.
@article{b275adfe40cf40c2b75735203dd7edee,
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 = "10",
day = "21",
doi = "10.1021/ol202248x",
language = "English",
volume = "13",
pages = "5568--5571",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=80054690764&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054690764&partnerID=8YFLogxK

U2 - 10.1021/ol202248x

DO - 10.1021/ol202248x

M3 - Article

VL - 13

SP - 5568

EP - 5571

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -