Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Methodology Development

Background:

• Cycloalkyl-fused naphthalenes are valuable structural motifs.
• Conventional synthetic methods for these compounds are often inefficient or limited.
• Novel approaches are needed for accessing these complex scaffolds.

Purpose of the Study:

• To develop an efficient and versatile method for synthesizing cycloalkyl-fused naphthalenes.
• To explore the scope of the reaction with different tethered substrates.
• To establish a one-pot procedure for polysubstituted naphthalene synthesis.

Main Methods:

• Utilizing [4 + 2]-cycloaddition/decarboxylative aromatization of alkyne-tethered aryne insertion adducts.
• Employing a reaction pathway involving benzopyrylium intermediate formation, intramolecular cycloaddition, and decarboxylation.
• Adapting the method for allene-tethered substrates.

Main Results:

• Efficient synthesis of cycloalkyl-fused naphthalenes was achieved.
• The reaction pathway was elucidated, involving key intermediates and transformations.
• The method demonstrated compatibility with both alkyne- and allene-tethered substrates.
• A one-pot synthesis of polysubstituted naphthalenes was successfully developed with good yields.

Conclusions:

• A novel and efficient synthetic strategy for cycloalkyl-fused naphthalenes has been established.
• The developed method offers a valuable alternative to conventional synthetic approaches.
• The one-pot procedure provides a streamlined route to polysubstituted naphthalene derivatives.