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PreprintCC BYChemRxiv

The Critical Role of Water in Safe, Scalable Diboron-Mediated Nitro Reductions .

  • Yilin Cao1
  • Matthew Joannou1
  • Michael Mandler2
  • Sergey Melnikov1
  • Iulia Teleuca2
  • Shasha Zhang1
  • Gregory Beutner1
  1. 1Chemical Process Development, Bristol Myers Squibb, 1 Squibb Drive, New Brunswick, NJ, United States, 08903
  2. 2Bristol Myers Squibb Therapeutic Discovery Sciences, P.O. Box 4000, Princeton, New Jersey, 08543
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Abstract

The use of diboron compounds for nitro group reduction, an essential transformation in the synthesis of a wide range of nitrogen-containing functional groups, offers an attractive alternative to traditional methods like hydrogenation and dissolving metal reduction. This method has seen limited uptake in the literature despite avoiding transition metals and specialized equipment. Using a combination of reaction calorimetry and kinetic analysis, careful selection of the reaction solvent, diboron source, and inclusion of water enabled the identification of safe and simple conditions for reduction of nitro groups. The scope of the reaction is broad under mild conditions where water plays a critical role in driving reactivity while maintaining wide safety margins.

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Cite

BibTeXRIS
BibTeX
@misc{cao2026critical,
  title = {{The Critical Role of Water in Safe, Scalable Diboron-Mediated Nitro Reductions .}},
  author = {Yilin Cao and Matthew Joannou and Michael Mandler and Sergey Melnikov and Iulia Teleuca and Shasha Zhang and Gregory Beutner},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15009744/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009744/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - The Critical Role of Water in Safe, Scalable Diboron-Mediated Nitro Reductions .
AU  - Yilin Cao
AU  - Matthew Joannou
AU  - Michael Mandler
AU  - Sergey Melnikov
AU  - Iulia Teleuca
AU  - Shasha Zhang
AU  - Gregory Beutner
PY  - 2026
DA  - 2026/10/01
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009744/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009744/v1
AB  - The use of diboron compounds for nitro group reduction, an essential transformation in the synthesis of a wide range of nitrogen-containing functional groups, offers an attractive alternative to traditional methods like hydrogenation and dissolving metal reduction. This method has seen limited uptake in the literature despite avoiding transition metals and specialized equipment. Using a combination of reaction calorimetry and kinetic analysis, careful selection of the reaction solvent, diboron source, and inclusion of water enabled the identification of safe and simple conditions for reduction of nitro groups. The scope of the reaction is broad under mild conditions where water plays a critical role in driving reactivity while maintaining wide safety margins.
ER  -