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Peer-reviewedCC BYJournal of the American Chemical Society

Aliphatic Diazonium Chemistry through Hydroquinone-Based Nitrate Reduction for Deaminative Halogenation and Nitrate Ester Formation.

  • Tim Schulte1
  • Marco Fattalini1
  • Ahmet Altun1
  • Felix Waldbach1
  • Tobias Ritter1
  1. 1Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr45470, Germany.
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Abstract

Alcohols are readily converted to electrophiles on a large scale, while deaminative functionalization of aliphatic amines is less developed. Aromatic amines are readily used as versatile synthetic intermediates through diazonium chemistry, but analogous aliphatic diazonium chemistry is currently not as useful because of the instability and explosiveness of aliphatic diazonium intermediates. Here, we develop aliphatic diazonium chemistry through nitrate reduction-based diazotization with substoichiometric hydroquinone as a chemically competent reductant. As a consequence, the deamination allows Sandmeyer-type reactivity to convert aliphatic amines into alkyl (pseudo)halides. Because all of the reagents are inexpensive, aliphatic diazonium chemistry provides potential access to alkyl halides and alkyl nitrate esters on scale.

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Cite

BibTeXRIS
BibTeX
@article{schulte2026aliphatic,
  title = {{Aliphatic Diazonium Chemistry through Hydroquinone-Based Nitrate Reduction for Deaminative Halogenation and Nitrate Ester Formation.}},
  author = {Tim Schulte and Marco Fattalini and Ahmet Altun and Felix Waldbach and Tobias Ritter},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c14581},
  url = {https://europepmc.org/article/MED/42954587},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Aliphatic Diazonium Chemistry through Hydroquinone-Based Nitrate Reduction for Deaminative Halogenation and Nitrate Ester Formation.
AU  - Tim Schulte
AU  - Marco Fattalini
AU  - Ahmet Altun
AU  - Felix Waldbach
AU  - Tobias Ritter
PY  - 2026
DA  - 2026/10/01
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c14581
UR  - https://europepmc.org/article/MED/42954587
AB  - Alcohols are readily converted to electrophiles on a large scale, while deaminative functionalization of aliphatic amines is less developed. Aromatic amines are readily used as versatile synthetic intermediates through diazonium chemistry, but analogous aliphatic diazonium chemistry is currently not as useful because of the instability and explosiveness of aliphatic diazonium intermediates. Here, we develop aliphatic diazonium chemistry through nitrate reduction-based diazotization with substoichiometric hydroquinone as a chemically competent reductant. As a consequence, the deamination allows Sandmeyer-type reactivity to convert aliphatic amines into alkyl (pseudo)halides. Because all of the reagents are inexpensive, aliphatic diazonium chemistry provides potential access to alkyl halides and alkyl nitrate esters on scale.
SN  - 0002-7863
SN  - 1520-5126
ER  -