Access to Polysulfides through Photocatalyzed Dithiosulfonylation

Area of Science:

• Organic Chemistry
• Photocatalysis
• Synthetic Methodology

Background:

• Difunctionalization of unsaturated compounds is crucial in organic synthesis.
• Developing atom-economical and selective methods remains a challenge.
• Dithiosulfonate reagents offer unique reactivity patterns.

Purpose of the Study:

• To establish a general photocatalyzed difunctionalization method.
• To utilize dithiosulfonate reagents (ArSO2-SSR) for efficient C-S bond formation.
• To explore the synthetic utility of the generated dithiosulfonylated products.

Main Methods:

• Photocatalysis with dithiosulfonate reagents.
• Broad substrate scope including alkenes, dienes, alkynes, 1,3-enynes, and [1.1.1]propellane.
• Gram-scale reaction optimization.

Main Results:

• Successful photocatalyzed difunctionalization with high stereoselectivity and regioselectivity.
• Broad substrate scope demonstrated.
• Dithiosulfonylated styrene identified as a practical nucleophilic disulfuration reagent.
• Reactions proceed under mild conditions with improved atom economy.

Conclusions:

• The developed method provides a versatile and efficient route for dithiosulfonylation.
• The study expands the utility of dithiosulfonate reagents in photocatalysis.
• The generated products are valuable intermediates for further synthetic applications.