Nitrate reduction enables safer aryldiazonium chemistry

Mateos, Javier; Schulte, Tim; Behera, Deepak; Leutzsch, Markus; Altun, Ahmet; Sato, Takuma; Waldbach, Felix; Schnegg, Alexander; Neese, Frank; Ritter, Tobias

doi:10.1126/science.adn7006

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Nitrate reduction enables safer aryldiazonium chemistry

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

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

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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;

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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;

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

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引用

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

引用: https://hdl.handle.net/21.11116/0000-000F-3D05-8

要旨

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.