A practical arylation of diazonium salts with diarylzinc reagents has been developed, thus affording straightforward access to non-symmetric azoarenes. Moreover, the user-friendly solid arylzinc pivalates can also undergo nucleophilic Csp-N bond formation. Mild conditions, transition metal-free process, broad substrate scope and functional group compatibility illustrate the synthetic utility of the reaction.
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Single Step Synthesis of Non-symmetric Azoarenes Using Buchwald-Hartwig Amination.
ACS Omega
November 2024
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice 53210, The Czech Republic.
Aromatic azo compounds stand as a highly sought-after class of substances owing to their extensive array of applications across various fields. Despite their significance, their synthesis often presents challenges, requiring either multistep reactions or being restricted to specific substrate types. In this study, we are showing the universality and mechanistic aspects of a one-step approach for synthesis of nonsymmetrical azoarenes via the Buchwald-Hartwig amination reaction of (pseudo)haloaromatics with arylhydrazines, conducted in the presence of atmospheric oxygen.
View Article and Find Full Text PDFOrganozincs for versatile synthesis of non-symmetric azoarenes.
Org Biomol Chem
July 2023
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Ren-Ai Road 199, 215123 Suzhou, P. R. China.
A practical arylation of diazonium salts with diarylzinc reagents has been developed, thus affording straightforward access to non-symmetric azoarenes. Moreover, the user-friendly solid arylzinc pivalates can also undergo nucleophilic Csp-N bond formation. Mild conditions, transition metal-free process, broad substrate scope and functional group compatibility illustrate the synthetic utility of the reaction.
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Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.
The photoswitchable motif of azobenzenes is of great importance across the life and materials sciences. This maintains a constant demand for their efficient synthesis, especially that of non-symmetric derivatives. We disclose here a general strategy for their synthesis through an unprecedented C(sp )-N(sp ) cross-coupling where functionalized aryl-substituted diazenes masked with a silyl group are employed as diazenyl pronucleophiles.
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