Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution

James Clayton; Jonathan Clayden

doi:10.1016/j.tetlet.2011.02.091

Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution

James Clayton, Jonathan Clayden

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

Abstract

Treatment of 4-, 3- or 2-aryl-4,5-diphenyloxazolines with isopropyllithium gives the products of dearomatising addition, fluorine-directed lithiation or nucleophilic aromatic substitution of fluoride depending on substitution pattern and conditions. In the case of the 4-fluoroaryl substrates, fluorinated 1,4-cyclohexadiene may be obtained in good yield. © 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2436-2439
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2011.02.091
Publication status	Published - 11 May 2011

Keywords

Carbolithiation
Dearomatisation
Metallation
Organofluorine chemistry
Oxazoline
Synthesis

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10.1016/j.tetlet.2011.02.091

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title = "Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution",

abstract = "Treatment of 4-, 3- or 2-aryl-4,5-diphenyloxazolines with isopropyllithium gives the products of dearomatising addition, fluorine-directed lithiation or nucleophilic aromatic substitution of fluoride depending on substitution pattern and conditions. In the case of the 4-fluoroaryl substrates, fluorinated 1,4-cyclohexadiene may be obtained in good yield. {\textcopyright} 2011 Elsevier Ltd. All rights reserved.",

keywords = "Carbolithiation, Dearomatisation, Metallation, Organofluorine chemistry, Oxazoline, Synthesis",

author = "James Clayton and Jonathan Clayden",

year = "2011",

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doi = "10.1016/j.tetlet.2011.02.091",

language = "English",

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T1 - Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution

AU - Clayton, James

AU - Clayden, Jonathan

PY - 2011/5/11

Y1 - 2011/5/11

N2 - Treatment of 4-, 3- or 2-aryl-4,5-diphenyloxazolines with isopropyllithium gives the products of dearomatising addition, fluorine-directed lithiation or nucleophilic aromatic substitution of fluoride depending on substitution pattern and conditions. In the case of the 4-fluoroaryl substrates, fluorinated 1,4-cyclohexadiene may be obtained in good yield. © 2011 Elsevier Ltd. All rights reserved.

AB - Treatment of 4-, 3- or 2-aryl-4,5-diphenyloxazolines with isopropyllithium gives the products of dearomatising addition, fluorine-directed lithiation or nucleophilic aromatic substitution of fluoride depending on substitution pattern and conditions. In the case of the 4-fluoroaryl substrates, fluorinated 1,4-cyclohexadiene may be obtained in good yield. © 2011 Elsevier Ltd. All rights reserved.

KW - Carbolithiation

KW - Dearomatisation

KW - Metallation

KW - Organofluorine chemistry

KW - Oxazoline

KW - Synthesis

U2 - 10.1016/j.tetlet.2011.02.091

DO - 10.1016/j.tetlet.2011.02.091

M3 - Article

VL - 52

SP - 2436

EP - 2439

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 19

ER -

Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution

Abstract

Keywords

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