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
coupling
