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Synthesis 2018; 50(12): 2359-2366
DOI: 10.1055/s-0036-1591969
DOI: 10.1055/s-0036-1591969
paper
Synthesis of Aromatic Disulfonic Acids for Water-Soluble Dibenzothiophene Derivatives
This work was supported by grants CHE-1255270 from the National Science Foundation and donors to the Herman Frasch Foundation.Further Information
Publication History
Received: 17 January 2018
Accepted after revision: 27 February 2018
Publication Date:
12 April 2018 (online)
Abstract
There is a need for efficient methods for the synthesis of water-soluble dibenzothiophene (DBT) and dibenzothiophene S-oxide (DBTO) derivatives to allow for the study of atomic oxygen in biological applications. Attaining water-solubility of aromatic compounds is effectively achieved through functionalization with sulfonic acid groups. Three approaches for the synthesis were considered. An indirect approach was unsuccessful. A modular approach was found to be highly effective for one DBTO disulfonic acid derivative (>99% pure). The direct approach was the most straightforward and highest-yielding route. Additionally, a highly effective, scalable, and improved purification method was identified for disulfonic acid DBT and DBTO derivatives, allowing for the isolation of positional isomers and other modifications by using reverse-phase high-performance flash chromatography.
Key words
sulfonic acids - sulfonation - sulfoxides - sulfides - dibenzothiophene - Suzuki couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591969.
- Supporting Information
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