Organosulfur compounds have a broad range of applications in the fields of medicinal chemistry and materials science. For the convenient access to these compounds, thiosulfonates have attracted attention as useful electrophilic sulfur surrogates, which are transformable into various organosulfur compounds in mild conditions without unpleasant odor. In spite of the utility, the preparation of S-aryl thiosulfonates through C−S bond formation are still limited. In this context, we conceived that the selective activation of morpholino group of Mor-SS-Ts using TFA could enable the efficient preparation of S-aryl thiosulfonates. Herein, we report the TFA mediated thiosulfonate synthesis from electron-rich arenes with Mor-SS-Ts. This reaction exhibited a broad substrate scope, which allowed for the convenient synthesis of diverse aryl sulfides from easily available starting materials.

TFA mediated preparation of S-aryl thiosulfonates from electron-rich arenes using Mor-SS-Ts

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.