Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Photochemistry

Background:

• Visible-light photocatalysis has emerged as a powerful tool in organic synthesis.
• Three-component reactions offer atom economy and efficiency in constructing complex molecules.
• Diazo compounds are versatile precursors for carbene generation.

Purpose of the Study:

• To develop a novel visible-light-promoted three-component reaction for imide synthesis.
• To utilize acceptor-only diazo compounds and nitriles for efficient carbene generation and trapping.
• To explore the synthetic utility of the resulting imide products.

Main Methods:

• A three-component reaction involving diazo compounds, nitriles, and carboxylic acids under visible light irradiation.
• Utilizing acceptor-only diazo compounds as carbene precursors.
• Employing nitriles as carbene-trapping reagents to form nitrile ylides.

Main Results:

• A wide range of imide products were synthesized in good to excellent yields.
• The reaction conditions were optimized for efficient imide formation.
• Gram-scale synthesis of imide products was successfully achieved.

Conclusions:

• The reported visible-light-promoted reaction provides an efficient route to diverse imide products.
• The synthesized imides serve as valuable intermediates for constructing isoquinoline-1,3(2H,4H)-dione derivatives.
• This methodology offers a practical and valuable approach in synthetic organic chemistry.