Stereospecific Acylative Suzuki-Miyaura Cross-Coupling: General Access to Optically Active α-Aryl Carbonyl Compounds

Area of Science:

• Organic Chemistry
• Catalysis
• Stereoselective Synthesis

Background:

• Chiral ketones and carboxylic acid derivatives are valuable synthetic targets.
• Stereospecific synthesis of these compounds remains challenging.

Purpose of the Study:

• To develop a novel strategy for stereospecific Pd-catalyzed acylative cross-coupling.
• To enable facile access to enantiomerically enriched chiral ketones and carboxylic acid derivatives.

Main Methods:

• Palladium-catalyzed acylative cross-coupling reaction.
• Utilized enantiomerically enriched alkylboron compounds.
• Employed a sterically encumbered and electron-rich phosphine ligand.

Main Results:

• Achieved a novel stereospecific Pd-catalyzed acylative cross-coupling protocol.
• Demonstrated extremely high enantiospecificity in the reaction.
• Synthesized valuable chiral ketones and carboxylic acid derivatives.

Conclusions:

• The developed protocol provides facile access to challenging chiral compounds.
• A sterically encumbered, electron-rich phosphine ligand is crucial for success.
• A unique, noncovalent interaction-assisted transmetalation mechanism was identified.