Recent progress in (hetero)arene cation radical-based heteroarene modification

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Cation radicals of arenes and heteroarenes are key intermediates in organic synthesis.
• Their generation via electrochemical, photochemical, or chemical oxidation is well-established.
• These reactive species can be intercepted by nucleophiles to form new carbon-carbon or carbon-heteroatom bonds.

Purpose of the Study:

• To review recent advances in heteroarene modification using in situ generated cation radicals.
• To highlight the scope and versatility of this synthetic strategy.
• To cover developments from 2010 to 2020.

Main Methods:

• Generation of (hetero)arene cation radicals through various oxidation methods.
• Nucleophilic addition to the in situ generated cation radicals.
• Synthesis of functionalized heteroarenes.

Main Results:

• Demonstration of diverse heteroarene modifications.
• Formation of structurally complex molecules.
• Expansion of synthetic methodologies for heteroarene construction.

Conclusions:

• In situ generated (hetero)arene cation radicals are a powerful tool for heteroarene functionalization.
• This strategy allows for the construction of diverse and highly functionalized molecules.
• Significant progress has been made in this field between 2010 and 2020.