Synthesis of Polysubstituted Vinyl Sulfones by Direct C-S Cross-Coupling

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• Vinyl sulfones possess valuable chemical properties and biological activity.
• Synthesizing diverse vinyl sulfone analogs is challenging, limiting their applications.

Purpose of the Study:

• To develop a novel, efficient, and selective method for synthesizing polysubstituted vinyl sulfones.
• To overcome limitations in creating diverse vinyl sulfone analogs.

Main Methods:

• Utilized N-iodosuccinimide (NIS) as a dual promoter for sulfonation and elimination reactions.
• Employed a mild protocol for late-stage vinyl sulfonation of complex molecules.
• Conducted competition experiments to understand sulfonyl radical reactivity.

Main Results:

• Successfully synthesized over 70 diverse polysubstituted vinyl sulfone analogs.
• Demonstrated broad applicability, efficiency, selectivity, and functional group tolerance.
• Gained insights into the reactivity of sulfonyl radicals with various C-C multiple bonds.

Conclusions:

• The developed method simplifies the synthesis of vinyl sulfones.
• This protocol enables the modification of complex natural products and advanced materials.
• Offers a versatile tool for accessing a wide range of vinyl sulfone derivatives.