Synthesis and photophysical properties of tetra- and pentaalkynylfluorobenzenes by Sonogashira reactions of novel iodofluorobenzenes

Muhammad Sharif; Aneela Maalik; Sebastian Reimann; Jamshed Iqbal; Tamás Patonay; Anke Spannenberg; Alexander Villinger; Peter Langer

doi:10.1016/j.tet.2012.10.049

Synthesis and photophysical properties of tetra- and pentaalkynylfluorobenzenes by Sonogashira reactions of novel iodofluorobenzenes

Muhammad Sharif, Aneela Maalik, Sebastian Reimann, Jamshed Iqbal, Tamás Patonay, Anke Spannenberg, Alexander Villinger, Peter Langer^*

^*Corresponding author for this work

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

12 Scopus citations

Abstract

1,2-Difluoro-3,4,5,6-tetraiodobenzene, 1,3-difluoro-2,4,5,6- tetraiodobenzene, 1,4-difluoro-2,3,5,6-tetraiodobenzene and 1-fluoro-2,3,4,5,6- pentaiodobenzene were prepared by oxidative iodination of fluorinated benzenes. Sonogashira cross-coupling reactions of these fluorinated periodobenzenes afforded fluorescent penta- and tetraalkynylfluorobenzenes in high yields.

Original language	English
Pages (from-to)	174-183
Number of pages	10
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.049
State	Published - 7 Jan 2013
Externally published	Yes

Bibliographical note

Funding Information:
Financial support by the DAAD , by the State of Pakistan and by the State of Mecklenburg-Vorpommern (scholarships for M.S.) and by the University of Rostock (INF scholarship for S.R.) is gratefully acknowledged. The work was also supported by the TÁMOP-4.2.1/B-09/KONV-2010-007 project. The project is implemented through the New Hungary Development Plan , co-financed by the European Social Fund and the European Regional Development Fund .

Keywords

Alkynes
Cross-coupling
Organofluorine compounds
Palladium
Sonogashira reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.10.049

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title = "Synthesis and photophysical properties of tetra- and pentaalkynylfluorobenzenes by Sonogashira reactions of novel iodofluorobenzenes",

abstract = "1,2-Difluoro-3,4,5,6-tetraiodobenzene, 1,3-difluoro-2,4,5,6- tetraiodobenzene, 1,4-difluoro-2,3,5,6-tetraiodobenzene and 1-fluoro-2,3,4,5,6- pentaiodobenzene were prepared by oxidative iodination of fluorinated benzenes. Sonogashira cross-coupling reactions of these fluorinated periodobenzenes afforded fluorescent penta- and tetraalkynylfluorobenzenes in high yields.",

keywords = "Alkynes, Cross-coupling, Organofluorine compounds, Palladium, Sonogashira reaction",

author = "Muhammad Sharif and Aneela Maalik and Sebastian Reimann and Jamshed Iqbal and Tam{\'a}s Patonay and Anke Spannenberg and Alexander Villinger and Peter Langer",

note = "Funding Information: Financial support by the DAAD , by the State of Pakistan and by the State of Mecklenburg-Vorpommern (scholarships for M.S.) and by the University of Rostock (INF scholarship for S.R.) is gratefully acknowledged. The work was also supported by the T{\'A}MOP-4.2.1/B-09/KONV-2010-007 project. The project is implemented through the New Hungary Development Plan , co-financed by the European Social Fund and the European Regional Development Fund .",

year = "2013",

month = jan,

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doi = "10.1016/j.tet.2012.10.049",

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T1 - Synthesis and photophysical properties of tetra- and pentaalkynylfluorobenzenes by Sonogashira reactions of novel iodofluorobenzenes

AU - Sharif, Muhammad

AU - Maalik, Aneela

AU - Reimann, Sebastian

AU - Iqbal, Jamshed

AU - Patonay, Tamás

AU - Spannenberg, Anke

AU - Villinger, Alexander

AU - Langer, Peter

N1 - Funding Information: Financial support by the DAAD , by the State of Pakistan and by the State of Mecklenburg-Vorpommern (scholarships for M.S.) and by the University of Rostock (INF scholarship for S.R.) is gratefully acknowledged. The work was also supported by the TÁMOP-4.2.1/B-09/KONV-2010-007 project. The project is implemented through the New Hungary Development Plan , co-financed by the European Social Fund and the European Regional Development Fund .

PY - 2013/1/7

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N2 - 1,2-Difluoro-3,4,5,6-tetraiodobenzene, 1,3-difluoro-2,4,5,6- tetraiodobenzene, 1,4-difluoro-2,3,5,6-tetraiodobenzene and 1-fluoro-2,3,4,5,6- pentaiodobenzene were prepared by oxidative iodination of fluorinated benzenes. Sonogashira cross-coupling reactions of these fluorinated periodobenzenes afforded fluorescent penta- and tetraalkynylfluorobenzenes in high yields.

AB - 1,2-Difluoro-3,4,5,6-tetraiodobenzene, 1,3-difluoro-2,4,5,6- tetraiodobenzene, 1,4-difluoro-2,3,5,6-tetraiodobenzene and 1-fluoro-2,3,4,5,6- pentaiodobenzene were prepared by oxidative iodination of fluorinated benzenes. Sonogashira cross-coupling reactions of these fluorinated periodobenzenes afforded fluorescent penta- and tetraalkynylfluorobenzenes in high yields.

KW - Alkynes

KW - Cross-coupling

KW - Organofluorine compounds

KW - Palladium

KW - Sonogashira reaction

UR - https://www.scopus.com/pages/publications/84870064128

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DO - 10.1016/j.tet.2012.10.049

M3 - Article

AN - SCOPUS:84870064128

SN - 0040-4020

VL - 69

SP - 174

EP - 183

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Synthesis and photophysical properties of tetra- and pentaalkynylfluorobenzenes by Sonogashira reactions of novel iodofluorobenzenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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