Indole-Quinoline Transmutation Enabled by a Formal Rhodium Carbynoid

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Skeleton editing offers a powerful strategy to streamline the synthesis of complex organic molecules.
• Developing new synthetic methodologies is crucial for advancing chemical synthesis and drug discovery.

Purpose of the Study:

• To develop a novel rhodium-catalyzed method for indole-quinoline transmutation.
• To achieve skeletal editing through single-carbon insertion into the indole C2-C3 bond.

Main Methods:

• Utilized a developed α-diazotrifluoroethyl sulfonium salt with rhodium catalysis.
• Employed a formal trifluoromethyl rhodium carbynoid intermediate (CF3C+=Rh).
• Conducted a computational study to elucidate the reaction mechanism.

Main Results:

• Achieved facile access to a diverse range of quinoline derivatives.
• Reported moderate to high yields for the synthesized quinolines.
• Demonstrated the potential for late-stage skeletal editing.

Conclusions:

• The presented protocol offers an efficient route for indole-quinoline transformation via skeletal editing.
• The method shows promise for applications in pharmaceutical and natural product synthesis.
• The rhodium-catalyzed carbynoid insertion provides a valuable tool for organic chemists.