Disulfide metathesis via sulfurMIDLINE HORIZONTAL ELLIPSISiodine interaction and photoswitchability

The idea of constitutional dynamic chemistry (CDC) and dynamic combinatorial chemistry (DCC) is widespread in the literature using the chemistry of disulfides. The synthesis of unsymmetrical diaryl disulfides is challenging due to the presence of a weak S-S bond. We report herein the synthesis of unsymmetrical diaryl disulfides from two symmetrical disulfides via a cross-metathesis reaction which was controlled by a weak sulfurMIDLINE HORIZONTAL ELLIPSISiodine (SMIDLINE HORIZONTAL ELLIPSISI) interaction. The unsymmetrical disulfides were stable in acetonitrile solution in the presence of N-iodosuccinimide (NIS), and found to be reversibly photoswitchable to the symmetrical disulfides under visible light irradiation.

Automated summary

By utilizing dynamic combinatorial chemistry, stable unsymmetrical diaryl disulfides were successfully synthesized under the control of weak sulfur-iodine interactions. These unsymmetrical disulfides exhibited reversible photo-switchable properties in organic solvents.