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Synthesis 2011(17): 2775-2780
DOI: 10.1055/s-0030-1260123
DOI: 10.1055/s-0030-1260123
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Preparation of Linear Aromatic Disulfonic Acids: New Linker Molecules for Metal-Organic Frameworks
Weitere Informationen
Received
10 May 2011
Publikationsdatum:
20. Juli 2011 (online)
Publikationsverlauf
Publikationsdatum:
20. Juli 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201117/lookinside/thumbnails/10.1055-s-0030-1260123-1.jpg)
Abstract
Four linear aromatic disulfonic acids were prepared, which are structurally similar to dicarboxylic acids commonly used as linker molecules for metal-organic frameworks. 4,4′-Biphenyldisulfonic acid was prepared in three steps from 4,4′-dibromobiphenyl (54% overall yield). Direct sulfonation of terphenyl gave the respective all-para-constituted disulfonic acid in 73% yield. Tolane-4,4′-disulfonic acid was obtained by a three-step sequence consisting of Sonogashira coupling, oxidative degradation of a thioester, and hydrolysis in 20% overall yield. By using a Glaser coupling, the bis(4-sulfophenyl)butadiyne was analogously prepared in 30% overall yield.
Key words
alkynes - arenes - sulfur - cross coupling - metal-organic frameworks
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