Base-Promoted Nucleophile Addition to Arynes Generated from Triaryloxonium Salts

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Nucleophilic addition reactions are fundamental in organic synthesis.
• Aryne chemistry offers unique pathways for C-C and C-heteroatom bond formation.
• Efficient synthesis of functionalized heterocycles and organic molecules remains a key challenge.

Purpose of the Study:

• To develop a facile and efficient method for synthesizing various aryl-substituted organic compounds.
• To explore the utility of oxonium aryne precursors in nucleophilic addition reactions.
• To demonstrate the broad applicability of the developed protocol for diverse synthetic targets.

Main Methods:

• Nucleophilic addition of oxonium aryne precursors to various nucleophiles.
• Utilized carboxylic acids, isocyanides, sulfoxonium ylides, mercaptans, trifluoromethyl silver, and halogenated quinolines/isoquinolines as reaction partners.
• Employed mild reaction conditions to ensure high yields and functional group tolerance.

Main Results:

• Successfully synthesized aryl-substituted esters, amides, α-aryl sulfoxonium ylides, thioethers, aryl-quinolinones, and aryl-isoquinolinones.
• Achieved high yields and demonstrated excellent functional group tolerance.
• Confirmed the feasibility of scale-up synthesis and explored potential applications.

Conclusions:

• A versatile and efficient synthetic methodology has been established for aryl-substituted compounds.
• The developed protocol offers a mild and high-yielding route applicable to a wide range of substrates.
• The method holds promise for the synthesis of complex organic molecules and pharmaceutical intermediates.