Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis

Area of Science:

• Organic Chemistry
• Catalysis
• Medicinal Chemistry

Background:

• Diaryl ethers are vital structural motifs found in numerous pharmaceuticals and natural products.
• Conventional synthesis of diaryl ethers often relies on metal-catalyzed cross-coupling reactions of aryl halides and phenols.
• Developing efficient and versatile synthetic methodologies for diaryl ethers remains an active area of research.

Purpose of the Study:

• To develop a novel catalytic method for the synthesis of diaryl ethers.
• To establish an efficient decarbonylative etherification of aromatic esters.
• To provide a scalable and high-yielding route to diaryl ethers.

Main Methods:

• Utilized a palladium or nickel catalyst in conjunction with a specialized diphosphine ligand.
• Employed a catalytic decarbonylative etherification strategy.
• Investigated both intramolecular and intermolecular cross-etherification reactions.

Main Results:

• Successfully synthesized various diaryl ethers with excellent yields.
• Demonstrated the scalability of the reaction to gram scale.
• Showcased the method's applicability in both intramolecular cyclizations and cross-etherifications with diverse phenols.

Conclusions:

• The developed catalytic decarbonylative etherification provides an effective new route to diaryl ethers.
• This method offers a valuable alternative to existing synthetic strategies for diaryl ether construction.
• The reaction's efficiency, scalability, and versatility make it a significant advancement in organic synthesis.