One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene

Muhammad Sharif; Muhammad Zeeshan; Sebastian Reimann; Alexander Villinger; Peter Langer

doi:10.1016/j.tetlet.2010.03.067

One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene

Muhammad Sharif, Muhammad Zeeshan, Sebastian Reimann, Alexander Villinger, Peter Langer^*

^*Corresponding author for this work

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

33 Scopus citations

Abstract

The Suzuki-Miyaura reaction of 1,4-dibromo-2-fluorobenzene with two equivalents of arylboronic acids gave fluorinated para-terphenyls. The reaction with 1 equiv of arylboronic acid resulted in site-selective formation of biphenyls. The one-pot reaction of 1,4-dibromo-2-fluorobenzene with two different arylboronic acids afforded fluorinated para-terphenyls containing two different terminal aryl groups.

Original language	English
Pages (from-to)	2810-2812
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2010.03.067
State	Published - 26 May 2010
Externally published	Yes

Bibliographical note

Funding Information:
We are grateful to Mr. Obaid-ur-Rahman Abid and to Mr. Rasheed Ahmad Khera for their help. Financial support by the DAAD (scholarships for M.S. and M.Z.) and by the University of Rostock (scholarship of the interdisciplinary faculty of the University of Rostock for S.R.) is gratefully acknowledged.

Keywords

Catalysis
Organofluorine compounds
Palladium
Site-selectivity
Suzuki-Miyaura reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene",

abstract = "The Suzuki-Miyaura reaction of 1,4-dibromo-2-fluorobenzene with two equivalents of arylboronic acids gave fluorinated para-terphenyls. The reaction with 1 equiv of arylboronic acid resulted in site-selective formation of biphenyls. The one-pot reaction of 1,4-dibromo-2-fluorobenzene with two different arylboronic acids afforded fluorinated para-terphenyls containing two different terminal aryl groups.",

keywords = "Catalysis, Organofluorine compounds, Palladium, Site-selectivity, Suzuki-Miyaura reaction",

author = "Muhammad Sharif and Muhammad Zeeshan and Sebastian Reimann and Alexander Villinger and Peter Langer",

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month = may,

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doi = "10.1016/j.tetlet.2010.03.067",

language = "English",

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pages = "2810--2812",

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AU - Sharif, Muhammad

AU - Zeeshan, Muhammad

AU - Reimann, Sebastian

AU - Villinger, Alexander

AU - Langer, Peter

N1 - Funding Information: We are grateful to Mr. Obaid-ur-Rahman Abid and to Mr. Rasheed Ahmad Khera for their help. Financial support by the DAAD (scholarships for M.S. and M.Z.) and by the University of Rostock (scholarship of the interdisciplinary faculty of the University of Rostock for S.R.) is gratefully acknowledged.

PY - 2010/5/26

Y1 - 2010/5/26

N2 - The Suzuki-Miyaura reaction of 1,4-dibromo-2-fluorobenzene with two equivalents of arylboronic acids gave fluorinated para-terphenyls. The reaction with 1 equiv of arylboronic acid resulted in site-selective formation of biphenyls. The one-pot reaction of 1,4-dibromo-2-fluorobenzene with two different arylboronic acids afforded fluorinated para-terphenyls containing two different terminal aryl groups.

AB - The Suzuki-Miyaura reaction of 1,4-dibromo-2-fluorobenzene with two equivalents of arylboronic acids gave fluorinated para-terphenyls. The reaction with 1 equiv of arylboronic acid resulted in site-selective formation of biphenyls. The one-pot reaction of 1,4-dibromo-2-fluorobenzene with two different arylboronic acids afforded fluorinated para-terphenyls containing two different terminal aryl groups.

KW - Catalysis

KW - Organofluorine compounds

KW - Palladium

KW - Site-selectivity

KW - Suzuki-Miyaura reaction

UR - https://www.scopus.com/pages/publications/77950954383

U2 - 10.1016/j.tetlet.2010.03.067

DO - 10.1016/j.tetlet.2010.03.067

M3 - Article

AN - SCOPUS:77950954383

SN - 0040-4039

VL - 51

SP - 2810

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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