Light-Driven EDA-APEX Approach: A One-Pot Access to Phenanthrenes and Naphthalenes

Area of Science:

• Organic Chemistry
• Photochemistry
• Synthetic Methodology

Background:

• Phenanthrenes and naphthalene derivatives are important structural motifs in various organic compounds.
• Existing synthetic routes often require transition metals or harsh conditions.

Purpose of the Study:

• To develop a novel, efficient, and metal-free method for synthesizing phenanthrenes and naphthalenes.
• To explore a light-driven annulative π-extension (APEX) strategy.

Main Methods:

• A transition-metal-free, light-driven annulative π-extension (APEX) reaction.
• Anion-π-initiation and O2-mediated oxidation.
• One-pot synthesis avoiding pre-functionalization.

Main Results:

• High yields of phenanthrenes (up to 95%) with excellent regioselectivity.
• Successful synthesis of diverse substituted phenanthrenes and naphthalenes.
• Demonstration of a metal-free, one-pot synthetic approach.

Conclusions:

• The developed APEX reaction provides a powerful and sustainable route to phenanthrene and naphthalene derivatives.
• This method offers advantages in terms of efficiency, substrate scope, and environmental impact.