Polyynes to Polycycles: Domino Reactions Forming Polyfused Chalcogenophenes

Area of Science:

• Organic Chemistry
• Heterocyclic Chemistry
• Materials Science

Background:

• Polyfused heterocyclic compounds are crucial building blocks in organic electronics and medicinal chemistry.
• Efficient synthetic routes to complex polyfused chalcogenophenes are limited.

Purpose of the Study:

• To develop a facile one-step method for synthesizing polyfused chalcogenophenes.
• To explore the scope and conditions for generating thiophene, selenophene, and tellurophene ring systems.

Main Methods:

• Utilized polyelectrophilic cyclization of polyynes.
• Employed the ambiphilic reagent methylaluminum chloride (MeACl) where A represents sulfur (S), selenium (Se), or tellurium (Te).

Main Results:

• Successfully synthesized polyfused chalcogenophenes in a single step.
• Generated up to four new fused rings, including thiophenes, selenophenes, and tellurophenes.
• The reactions proceeded under mild conditions.

Conclusions:

• The developed method offers a straightforward and efficient approach to polyfused chalcogenophenes.
• This synthesis opens avenues for new materials with potential applications in electronics and beyond.