Continuous Pd-Catalyzed Carbonylative Cyclization Using Iron Pentacarbonyl as a CO Source.

Area of Science:

• Organic Chemistry
• Flow Chemistry
• Catalysis

Background:

• Carbonylation reactions are crucial in organic synthesis.
• Traditional methods often require specialized equipment or harsh conditions.
• Developing efficient and scalable flow carbonylation is highly desirable.

Purpose of the Study:

• To disclose a continuous flow carbonylation reaction.
• To utilize iron pentacarbonyl as a carbon monoxide (CO) source in flow systems.
• To enable scalable synthesis of valuable compounds, including natural products.

Main Methods:

• Development of a continuous flow carbonylation protocol using iron pentacarbonyl.
• Optimization of reaction conditions for flow equipment.
• Application of the optimized method to the synthesis of a natural compound.
• Demonstration of a flow palladium-catalyzed carbonylation of aryl halides.

Main Results:

• Successful implementation of a continuous flow carbonylation reaction.
• Scalable synthesis of a natural compound from African civet cat pheromone.
• Demonstration of the versatility of the flow system for aryl halide carbonylation.
• Iron pentacarbonyl effectively serves as a CO surrogate in flow.

Conclusions:

• The developed continuous flow carbonylation is efficient and scalable.
• This method offers a practical approach for synthesizing complex molecules.
• The methodology is adaptable for various carbonylation transformations in flow.