Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization

Area of Science:

• Organic Chemistry
• Photoredox Catalysis
• Synthetic Methodology

Background:

• Destruction of aromatic rings typically requires harsh conditions and lacks selectivity.
• Selective partial dearomatization of fused arenes is difficult but offers a route to complex polycyclic structures.

Purpose of the Study:

• To develop a general organophotoredox method for chemo- and regioselective dearomatization of diverse polycyclic aromatic compounds.
• To enable the synthesis of complex polycyclic frameworks with high selectivity.

Main Methods:

• Utilized an organophotoredox catalysis approach.
• Employed a hydrogen atom transfer (HAT) agent to favor dearomatization.
• Manipulated the electronic properties of fused polycyclic arenes.

Main Results:

• Achieved chemo- and regioselective dearomatization of various polycyclic aromatics (quinolines, naphthalenes, etc.).
• Demonstrated the method's success in synthesizing biologically relevant molecules.
• Showcased late-stage skeletal remodeling for complex structure generation.

Conclusions:

• The developed organophotoredox method provides a selective and versatile route for dearomatization of fused arenes.
• This strategy facilitates the efficient construction of complex polycyclic architectures.
• The approach is applicable to synthesizing valuable targets and modifying complex structures.