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Visible-Light-Induced Flavin Catalysis: A Green Route to Naphtho[2,1-b]furans via an o-(Naphtho)quinone Intermediate.

Bhabani Sankar Lenka1, Rama Kant Mishra1, Debayan Sarkar1

  • 1Department of Chemistry, Indian Institute of Technology Indore, Indore, Madhya Pradesh 453552, India.

Organic Letters
|July 11, 2025
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Summary
This summary is machine-generated.

A novel green synthesis method for naphthofurans utilizes riboflavin tetraacetate as a photocatalyst. This aerobic approach is versatile, works with many substrates, and confirms a proposed reaction pathway involving o-(naphtho)quinone intermediates.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Green Chemistry

Background:

  • Naphthofuran synthesis is crucial in medicinal chemistry.
  • Existing methods often involve harsh conditions or toxic reagents.
  • Development of sustainable synthetic routes is highly desirable.

Purpose of the Study:

  • To develop a green, aerobic, and efficient method for naphthofuran synthesis.
  • To utilize a readily available photocatalyst for this transformation.
  • To elucidate the reaction mechanism.

Main Methods:

  • Photocatalysis using riboflavin tetraacetate under aerobic conditions.
  • Employing a diverse range of substrates with various functional groups.
  • Conducting control experiments to verify reaction intermediates.

Main Results:

  • Successful synthesis of naphthofurans using a green and aerobic protocol.
  • Demonstrated broad substrate scope and functional group tolerance.
  • Confirmed the involvement of o-(naphtho)quinone intermediates in the mechanism.

Conclusions:

  • Riboflavin tetraacetate is an effective photocatalyst for naphthofuran synthesis.
  • The developed method offers a sustainable alternative to traditional approaches.
  • The mechanistic studies support the proposed catalytic pathway.