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PreprintCC BYChemRxiv

Unified reductive synthesis of pyrrole and indole under acid-free conditions

  • Ruizhi Yang1,2
  • Changshu Wu1,2
  • Qiu Shi3,4
  • Wenbo H. Liu1,2
4 affiliations
  1. 1School of Chemistry
  2. 2Sun Yat-sen University
  3. 3College of Light Chemical Industry and Materials Engineering
  4. 4Shunde Polytechnic University
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Abstract

Reductive functionalization of nitrogen-bearing carboxylic acid derivatives represents a powerful yet underexplored platform for assembling value-added nitrogen heterocycles. Herein, we describe an iridium-catalyzed unified reductive manifold that converts acyclic hydrazides into pyrroles and indoles under acid-free conditions. This transformation realizes sigmatropic rearrangement via in-situ formed N,N’-dialkyl bisvinylhydrazine intermediates, circumventing key limitations of classic Piloty-Robinson and Fischer syntheses. Excellent functional-group compatibility and scale-up capability underscore its potential to expand the synthetic toolbox for carboxylic-derived nitrogen-containing molecules.

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Cite

BibTeXRIS
BibTeX
@misc{yang2026unified,
  title = {{Unified reductive synthesis of pyrrole and indole under acid-free conditions}},
  author = {Ruizhi Yang and Changshu Wu and Qiu Shi and Wenbo H. Liu},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010696/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010696/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Unified reductive synthesis of pyrrole and indole under acid-free conditions
AU  - Ruizhi Yang
AU  - Changshu Wu
AU  - Qiu Shi
AU  - Wenbo H. Liu
PY  - 2026
DA  - 2026/10/20
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010696/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010696/v1
AB  - Reductive functionalization of nitrogen-bearing carboxylic acid derivatives represents a powerful yet underexplored platform for assembling value-added nitrogen heterocycles. Herein, we describe an iridium-catalyzed unified reductive manifold that converts acyclic hydrazides into pyrroles and indoles under acid-free conditions. This transformation realizes sigmatropic rearrangement via in-situ formed N,N’-dialkyl bisvinylhydrazine intermediates, circumventing key limitations of classic Piloty-Robinson and Fischer syntheses. Excellent functional-group compatibility and scale-up capability underscore its potential to expand the synthetic toolbox for carboxylic-derived nitrogen-containing molecules.
ER  -