Photocatalytic Aminative Suzuki-Miyaura C(sp²)-N-C(sp³) Cross-Coupling

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Suzuki-Miyaura coupling is a vital tool for C-C bond formation.
• Conventional C(sp²)-C(sp³) coupling often yields direct linkages.
• Developing novel cross-coupling architectures remains an active research area.

Purpose of the Study:

• To introduce a novel photoinduced Suzuki-Miyaura coupling protocol.
• To achieve C(sp²)-N-C(sp³)-bridged structures via nitrene insertion.
• To optimize reaction conditions for efficiency and broad applicability.

Main Methods:

• Employing a photoinduced reaction strategy.
• Utilizing a nitrene reagent to redirect coupling pathways.
• Implementing a high-throughput screening approach (432 reactions) for parameter optimization.

Main Results:

• Successfully developed a photoinduced Suzuki-Miyaura C(sp²)-C(sp³) coupling protocol.
• Demonstrated the redirection of coupling toward C(sp²)-N-C(sp³)-bridged products.
• Identified optimal reaction parameters through extensive screening.

Conclusions:

• The developed protocol offers mild reaction conditions and convenient operation.
• The method exhibits good functional group tolerance.
• This work provides a foundation for new catalytic systems in cross-coupling reactions.