Article Dans Une Revue Journal of Organic Chemistry Année : 2024

Synthesis of Halogenated Dibenzo[1,2,6]triazonines and Late-Stage Functionalization of the Triazonine Ring

Résumé

Dibenzotriazonine is a new class of nine-membered cyclic azobenzenes, with a nitrogen atom embedded in the bridging chain. To enable future applications of this photoactive backbone, we propose in this study the synthesis of mono and dihalogenated triazonines, that allow the late-stage introduction of different functionalized aryl groups and heteroatoms (N, O, P) via palladium-catalyzed reactions. Indeed, different diphenylphosphoryl-triazonines were synthesized with functional groups such as carbamate or phenol. Bis(diphenylphosphoryl)phenyl-mono-and bis-carbamate-triazonines were also isolated in good yields.

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hal-04760995 , version 1 (30-10-2024)

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Vincent Delattre, Nawel Goual, Pascal Retailleau, Angela Marinetti, Arnaud Voituriez. Synthesis of Halogenated Dibenzo[1,2,6]triazonines and Late-Stage Functionalization of the Triazonine Ring. Journal of Organic Chemistry, 2024, 89 (15), pp.10939-10945. ⟨10.1021/acs.joc.4c01293⟩. ⟨hal-04760995⟩
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