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Wen-Jie Xiao1, Cheng-Xin Li1, Jing-Yi Lv1

  • 1Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.

Angewandte Chemie (International Ed. in English)
|July 15, 2024
PubMed
Summary
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ACS applied materials & interfaces·2025

Chemists developed a novel molecular editing reaction to transform pyrrole rings into benzene and naphthalene derivatives. This method utilizes a Diels-Alder and cheletropic reaction sequence, eliminating nitrogen gas for efficient ring conversion.

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Context:

  • Pyrrole rings are common heterocycles with limited direct synthetic routes to aromatic carbocycles.
  • Developing efficient methods for ring transformation is crucial in organic synthesis.

Purpose:

  • To develop a novel molecular editing reaction for the conversion of pyrrole rings into benzene and naphthalene derivatives.
  • To elucidate the reaction mechanism involving Diels-Alder and cheletropic steps.

Summary:

  • A sequential reaction pathway involving Diels-Alder cycloaddition followed by a cheletropic reaction was established for pyrrole ring transformation.
  • The elimination of a nitrogen atom as N2O from an N-bridged intermediate drives the reaction via a strain-releasing pathway.
  • This process yields substituted benzene and naphthalene derivatives.
Keywords:
late-stage functionalizationmolecular editingnitrogen deletionskeletal editingstrain-release

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Impact:

  • Provides a new synthetic strategy for accessing substituted benzene and naphthalene scaffolds from pyrrole precursors.
  • Offers a valuable tool for medicinal chemistry and materials science, enabling the synthesis of complex aromatic systems.