Base-Mediated Annulation Strategy to Naphthol Boronic Ester Derivatives.

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Homophthalic anhydrides are versatile building blocks in organic synthesis.
• Developing efficient methods for synthesizing substituted phenols is crucial.

Purpose of the Study:

• To develop a novel, regioselective annulation reaction for ortho-acylphenol derivatives.
• To explore the subsequent functionalization of these derivatives.

Main Methods:

• Base-promoted annulation reaction.
• Utilized homophthalic anhydrides and potassium ynone trifluoroborate salts.
• Chemoselective functionalization via cross-coupling, O-alkylation, and oxidative coupling.

Main Results:

• Achieved a convenient and regioselective synthesis of ortho-acylphenol derivatives.
• Demonstrated the versatility of the synthesized products through further chemical modifications.
• The reaction provides a straightforward route to complex phenolic structures.

Conclusions:

• The developed annulation reaction is an effective method for accessing ortho-acylphenol derivatives.
• The synthesized compounds serve as valuable intermediates for further synthetic elaborations.
• This work expands the synthetic utility of homophthalic anhydrides.