A Novel Approach for Synthesis of Functionalized Benzenethiol Equivalents

Unlocking Complex Sulfur Molecules A Novel Approach for Synthesis of Functionalized Benzenethiol Equivalents

2024-06-06 Source: Tokyo University of Science 3 min Reading Time

DÜPERTHAL Sicherheitstechnik GmbH & Co. KG

Organosulfur skeletons are crucial in many fields, including pharmaceuticals and electronics. Synthesizing organosulfur skeletons requires o-bromobenzenethiols. However, conventional methods face challenges due to quick oxidation and formation of highly reactive intermediates. In a new study, researchers from Japan developed a new method for synthesizing o-bromobenzenethiols from aryne intermediates via bromothiolation. This method can pave the way for the synthesis of new organosulfur compounds with applications in diverse fields.

Synthesizing o-bromobenzenethiols from aryne intermediates: This innovative method involves bromothiolation of aryne intermediates, resulting in the formation of highly functional o-bromobenzenethiols, which can be subsequently used to prepare diverse organosulfur compounds.(Source: Suguru Yoshida from Tokyo University of Science) — Synthesizing o-bromobenzenethiols from aryne intermediates: This innovative method involves bromothiolation of aryne intermediates, resulting in the formation of highly functional o-bromobenzenethiols, which can be subsequently used to prepare diverse organosulfur compounds.
(Source: Suguru Yoshida from Tokyo University of Science)

Organosulfur compounds, organic compounds containing sulfur, are vital in biological processes and research fields like pharmaceuticals, biomedical imaging, agriculture, and electronics. Compounds like phenothiazine, thianthrene and thienothiophene, containing organosulfur skeletons, play pivotal roles in these domains. Multiple methods have been developed that use o-bromobenzenethiols as the key component to synthesize these compounds. This is mainly owing to the high reactivities of the thiol (sulfur atom bonded to a hydrogen atom) and bromine moieties of o-bromobenzenethiols, compounds which contain a bromine atom attached to positions one or two (ortho position) in a benzene ring next to a sulfur atom.

Conventional methods to produce o-bromobenzenethiols involve addition of bromine to aniline, then using diazonium intermediates for addition of sulfur. This process poses challenges including selective addition of bromine at the ortho position, difficulty working with certain chemical groups, and the tendency of o-bromobenzenethiols to oxidize easily in air releasing unpleasant odors.

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