Universität zu Köln

Christoffers, Jens and Wickleder, Mathias S. ORCID: 0000-0002-8864-4227 (2020). Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids. Synlett, 31 (10). S. 945 - 953. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman-Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing moieties at an aromatic ring. Sulfonic acids are then accessed by oxidation of thiols, thioethers, or thioesters either directly with hydrogen peroxide or in two steps with chlorine (generated in situ from N-chlorosuccinimide/hydrochloric acid) to furnish sulfochlorides which are subsequently hydrolyzed. In the aliphatic series, secondary alcohols as starting materials are converted into thioethers, thioesters, or thiocarbonates by nucleophilic substitutions, which are also subsequently oxidized to furnish sulfonic acids.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Christoffers, Jens UNSPECIFIED UNSPECIFIED UNSPECIFIED Wickleder, Mathias S. UNSPECIFIED orcid.org/0000-0002-8864-4227 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-329824
DOI:	10.1055/s-0039-1691745
Journal or Publication Title:	Synlett
Volume:	31
Number:	10
Page Range:	S. 945 - 953
Date:	2020
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-2096
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Inorganic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language METAL-ORGANIC FRAMEWORKS; CATALYZED C-S; COORDINATION POLYMERS; CRYSTAL-STRUCTURE; DISULFONIC ACIDS; ARYL; CONVERSION; DESIGN; LINKER; REARRANGEMENT Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/32982