Swift C-C bond insertion by a 12-electron palladium(0) surrogate

Area of Science:

• Organometallic Chemistry
• Catalysis
• Organic Synthesis

Background:

• Selective C-C bond activation is crucial for catalysis but often requires harsh conditions.
• Previous research focused on rhodium and nickel catalysts for C-C bond activation.

Purpose of the Study:

• To report C-C insertion reactions using a novel 12-electron palladium(0) surrogate.
• To investigate the influence of ring strain and carbon hybridization on reactivity.
• To establish mild conditions for C-C bond functionalization catalysis.

Main Methods:

• Utilized a palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand.
• Studied reactions with benzonitrile, biphenylene, benzocyclobutenone, and naphtho[b]cyclopropene.
• Analyzed the effects of varying substrate ring strain and carbon hybridization (sp3, sp2, sp).

Main Results:

• Achieved quantitative C-C insertion reactions with the studied substrates.
• All reactions proceeded effectively at or below room temperature.
• Demonstrated the catalyst's ability to activate diverse C-C bonds.

Conclusions:

• The developed palladium-CAAC system enables mild and efficient C-C bond functionalization.
• This work expands the scope of catalytic C-C bond activation under accessible conditions.
• Presents new perspectives for developing sustainable catalytic processes.