Intramolecular aryl-aryl coupling via C-F bond activation tolerant towards C-I functionality

Area of Science:

• Organic Chemistry
• Synthetic Methodology
• Catalysis

Background:

• Aromatic carbon-fluorine (C-F) bonds are prevalent but notoriously stable.
• Activating C-F bonds typically requires harsh conditions or transition metal catalysts.
• Developing selective C-F bond activation is crucial for synthetic efficiency.

Purpose of the Study:

• To report a transition-metal-free method for activating aromatic C-F bonds.
• To achieve intramolecular aryl-aryl coupling using this activation.
• To demonstrate orthogonality with carbon-iodine (C-I) functionality.

Main Methods:

• Development of a novel reaction condition for C-F bond activation.
• Utilizing intramolecular coupling to form new aryl-aryl bonds.
• Testing the compatibility of the method with C-I bonds.

Main Results:

• Successful activation of a stable aromatic C-F bond without transition metals.
• Efficient intramolecular aryl-aryl coupling was achieved.
• The developed method showed high selectivity and was orthogonal to C-I bonds.

Conclusions:

• A new, transition-metal-free strategy for C-F bond activation has been established.
• This method provides a valuable approach for intramolecular aryl-aryl bond formation.
• The orthogonality to C-I functionality expands its synthetic utility.