Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes

Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temperature, can be stored for at least 20 days....

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Bibliographic Details
Published in:Tetrahedron 2018-09, Vol.74 (38), p.5289-5294
Main Authors: Thon, Daniel, Fürst, Michael C.D., Altmann, Lisa-Marie, Heinrich, Markus R.
Format: Article
Language:English
Subjects:
Biaryl
Carboamination
Carbohydroxylation
Diazonium
Radical reaction
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Summary:Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temperature, can be stored for at least 20 days. In addition, the slow melting of aryldiazonium-containing ice cubes can serve as an alternative to syringe pumps that are commonly used if a controlled addition of the diazonium salt to the reaction mixture is required. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.05.089