English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

Nitrate reduction enables safer aryldiazonium chemistry

MPS-Authors
/persons/resource/persons266601

Mateos,  Javier
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons259806

Schulte,  Tim
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University, ;

/persons/resource/persons298075

Behera,  Deepak
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University, ;

/persons/resource/persons132873

Leutzsch,  Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58397

Altun,  Ahmet
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons298077

Waldbach,  Felix
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216825

Neese,  Frank
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons198096

Ritter,  Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

Mateos, J., Schulte, T., Behera, D., Leutzsch, M., Altun, A., Sato, T., et al. (2024). Nitrate reduction enables safer aryldiazonium chemistry. Science, 384(6694), 446-452. doi:10.1126/science.adn7006.


Cite as: https://hdl.handle.net/21.11116/0000-000F-3D05-8
Abstract
Aryldiazonium salts remain a staple in organic synthesis and are still prepared largely in accord with the protocol developed in the 19th century. Because of the favorable reactivity that often cannot be achieved with other aryl(pseudo)halides, diazonium chemistry continues to grow. Facile extrusion of dinitrogen contributes to the desired reactivity but is also reason for safety concerns. Explosions have occurred since the discovery of these reagents and still result in accidents. In this study, we report a diazonium chemistry paradigm shift based on nitrate reduction using thiosulfate or dihalocuprates as electron donors that avoids diazonium accumulation. Because nitrate reduction is rate-limiting, aryldiazoniums are produced as fleeting intermediates, which results in a safer and often more efficient deaminative halogenation in a single step from anilines.