Tandem Suzuki Coupling/Intramolecular Oxetane Ring Opening to Form Polycyclic Ring Systems

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Tandem reactions offer efficient synthetic routes.
• Oxetane chemistry provides access to unique structural motifs.

Purpose of the Study:

• To develop a tandem one-pot reaction for synthesizing multicyclic systems.
• To utilize intramolecular oxetane ring opening following cross-coupling.
• To provide a convergent approach for scaffold generation.

Main Methods:

• A tandem reaction sequence involving cross-coupling and nucleophilic oxetane ring opening.
• Mild nucleophiles were employed for the ring-opening step.
• Computational analysis of conformers to explain reaction outcomes.

Main Results:

• Successful synthesis of diverse multicyclic ring systems.
• Formation of both carbon-carbon and carbon-heteroatom bonds in one pot.
• Generation of a pendant hydroxymethyl group for further functionalization.

Conclusions:

• The reported tandem reaction is a convergent and efficient method for accessing complex molecular architectures.
• Computational studies aid in understanding the stereochemical control and limitations of the cyclization process.