Oxidation of benzyl alcohols with difluoro(aryl)-λ3-bromane: formation of benzyl fluoromethyl ethers via oxidative rearrangement

Masahito Ochiai; Akira Yoshimura; Kazunori Miyamoto

doi:10.1016/j.tetlet.2009.06.042

Oxidation of benzyl alcohols with difluoro(aryl)-λ³-bromane: formation of benzyl fluoromethyl ethers via oxidative rearrangement

Masahito Ochiai, Akira Yoshimura, Kazunori Miyamoto

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Oxidative rearrangement of benzyl alcohols with difluoro(p-trifluoromethylphenyl)-λ³-bromane (5 × 10^-2 M) in chloroform at room temperature afforded aryl fluoromethyl ethers selectively in good yields, probably via 1,2-shift of aryl groups from benzylic carbon to oxygen atoms.

Original language	English (US)
Pages (from-to)	4792-4795
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2009.06.042
State	Published - Aug 18 2009
Externally published	Yes

Bibliographical note

Funding Information:
We gratefully acknowledge the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support in the form of a grant.

Keywords

Alcohol
Bromine
Ether
Hypervalent
Oxidation
Rearrangement

Publisher link

10.1016/j.tetlet.2009.06.042

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title = "Oxidation of benzyl alcohols with difluoro(aryl)-λ3-bromane: formation of benzyl fluoromethyl ethers via oxidative rearrangement",

abstract = "Oxidative rearrangement of benzyl alcohols with difluoro(p-trifluoromethylphenyl)-λ3-bromane (5 × 10-2 M) in chloroform at room temperature afforded aryl fluoromethyl ethers selectively in good yields, probably via 1,2-shift of aryl groups from benzylic carbon to oxygen atoms.",

keywords = "Alcohol, Bromine, Ether, Hypervalent, Oxidation, Rearrangement",

author = "Masahito Ochiai and Akira Yoshimura and Kazunori Miyamoto",

note = "Funding Information: We gratefully acknowledge the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support in the form of a grant. ",

year = "2009",

month = aug,

day = "18",

doi = "10.1016/j.tetlet.2009.06.042",

language = "English (US)",

volume = "50",

pages = "4792--4795",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Oxidation of benzyl alcohols with difluoro(aryl)-λ3-bromane

T2 - formation of benzyl fluoromethyl ethers via oxidative rearrangement

AU - Ochiai, Masahito

AU - Yoshimura, Akira

AU - Miyamoto, Kazunori

N1 - Funding Information: We gratefully acknowledge the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support in the form of a grant.

PY - 2009/8/18

Y1 - 2009/8/18

N2 - Oxidative rearrangement of benzyl alcohols with difluoro(p-trifluoromethylphenyl)-λ3-bromane (5 × 10-2 M) in chloroform at room temperature afforded aryl fluoromethyl ethers selectively in good yields, probably via 1,2-shift of aryl groups from benzylic carbon to oxygen atoms.

AB - Oxidative rearrangement of benzyl alcohols with difluoro(p-trifluoromethylphenyl)-λ3-bromane (5 × 10-2 M) in chloroform at room temperature afforded aryl fluoromethyl ethers selectively in good yields, probably via 1,2-shift of aryl groups from benzylic carbon to oxygen atoms.

KW - Alcohol

KW - Bromine

KW - Ether

KW - Hypervalent

KW - Oxidation

KW - Rearrangement

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U2 - 10.1016/j.tetlet.2009.06.042

DO - 10.1016/j.tetlet.2009.06.042

M3 - Article

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SN - 0040-4039

VL - 50

SP - 4792

EP - 4795

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -