Nickel-Catalyzed Reductive Arylalkylation via a Migratory Insertion/Decarboxylative Cross-Coupling Cascade

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Aryl iodides and unactivated alkenes are common building blocks in organic synthesis.
• Developing efficient methods for arylalkylation is crucial for constructing complex molecules.
• Traditional methods often require pregenerated organometallic reagents, limiting substrate scope and functional group tolerance.

Purpose of the Study:

• To develop a novel nickel-catalyzed reductive arylalkylation of unactivated alkenes.
• To utilize redox-active N-hydroxyphthalimide esters as alkyl sources.
• To achieve a cascade process merging migratory insertion and decarboxylative cross-coupling.

Main Methods:

• Nickel catalysis
• Reductive arylalkylation
• Cascade reaction involving migratory insertion and decarboxylative cross-coupling
• Use of N-hydroxyphthalimide esters as alkylating agents

Main Results:

• Successful synthesis of benzene-fused carbo- and heterocyclic compounds.
• High functional group tolerance observed.
• Avoidance of pregenerated organometallic reagents.
• Efficient merging of key catalytic steps in a cascade.

Conclusions:

• A versatile and efficient nickel-catalyzed method for arylalkylation has been established.
• The developed strategy enables the synthesis of diverse and complex molecular architectures.
• This approach offers a valuable alternative to existing methods, particularly for functionalized substrates.