Site-Selective Sonogashira Reactions of 1,4-Dibromo-2-fluorobenzene - Synthesis and Properties of Fluorinated Alkynylbenzenes | Health & Environmental Research Online (HERO)

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HERO ID

6910390

Reference Type

Journal Article

Title

Site-Selective Sonogashira Reactions of 1,4-Dibromo-2-fluorobenzene - Synthesis and Properties of Fluorinated Alkynylbenzenes

Author(s)

Reimann, S; Sharif, M; Hein, M; Villinger, A; Wittler, Kai; Ludwig, R; Langer, P; ,

Year

2012

Is Peer Reviewed?

Yes

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690

Publisher

WILEY-V C H VERLAG GMBH

Location

WEINHEIM

Issue

Page Numbers

604-615

Language

English

DOI

10.1002/ejoc.201100394

Web of Science Id

WOS:000299295700021

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84855951586&doi=10.1002%2fejoc.201100394&partnerID=40&md5=4eff9211c2f16150c2398d5fae8236b9
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Abstract

A variety of alkynyl-substituted fluorinated benzene derivatives have been prepared by Sonogashira cross-coupling reactions of 1,4-dibromo-2-fluorobenzene. The reactions proceed with very good site-selectivity in favor of the 4-position because of electronic and steric reasons. The regioselectivity is explained by the results of DFT calculations. The absorption and emission (fluorescence) properties of the products, mono-and dialkynylated fluorobenzenes, have been studied. In addition, the mesomorphic properties of the products have been investigated by polarization microscopy and differential scanning calorimetry. 1,4-Dialkynyl-2-fluorobenzenes show nematic liquid-crystalline properties over a long phase range.