meta-Substituted Diaryliodonium Salts Enabled Aryne 1,2,4'-Trifunctionalization

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Aryne chemistry is crucial for constructing complex organic molecules.
• Developing selective functionalization methods for arynes remains a significant challenge in organic synthesis.

Purpose of the Study:

• To develop a novel cascade reaction for the 1,2,4-trifunctionalization of arynes.
• To achieve sequential C-N, C-S, and para-selective C-C bond formation in a single synthetic operation.

Main Methods:

• Utilized meta-substituted diaryliodonium salts as precursors.
• Employed a reaction sequence involving a [5,5]-sigmatropic shift followed by a thia-Fries rearrangement.

Main Results:

• Successfully achieved 1,2,4-trifunctionalization of arynes.
• Demonstrated sequential C-N and C-S bond formation.
• Attained challenging para-selective C-C bond formation on the non-aryne aromatic ring.

Conclusions:

• The developed cascade reaction offers an efficient route to complex trifunctionalized aromatic compounds.
• This method provides a powerful tool for synthetic chemists, enabling the construction of intricate molecular architectures.