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

✍ Scribed by Sebastian Reimann; Muhammad Sharif; Martin Hein; Alexander Villinger; Kai Wittler; Ralf Ludwig; Peter Langer

Book ID
102831405
Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
891 KB
Volume
2012
Category
Article
ISSN
1434-193X

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✦ Synopsis

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.

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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 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 401 KB

## a b s t r a c t 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-fluorobenz