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General and Scalable Approach to A 2 B- and A 2 BC-Type Porphyrin Phosphonate Diesters

Abstract : A two-step reaction sequence for accessing meso-(dialkoxyphosphoryl) porphyrins from readily available trans-A(2)-type porphyrins was developed. This approach involves bromination and subsequent palladium-catalyzed phosphonylation. Optimal conditions for both steps were identified after exploration of various reaction parameters such as solvent, temperature and catalyst. A series of dialkoxyphosphoryl-substituted A2B-porphyrins Zn3(a-g) bearing electron-donating, electron-withdrawing or sterically bulky substituents at the meso-aryl groups were prepared in overall yields close to 40 %. These compounds, being air-stable and soluble in most organic solvents, are valuable synthetic intermediates because they can be readily transformed into functionalized trans-A(2)BC-type porphyrins through regioselective functionalization at the unsubstituted meso position of the macrocycle. Therefore, this approach offers considerable promise for application to the synthesis of trans-A(2)BC-type porphyrins, including water-soluble derivatives, push-pull chromophores and bis(porphyrin)s.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01429823
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : lundi 9 janvier 2017 - 11:06:20
Dernière modification le : mardi 14 juillet 2020 - 11:04:07

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Yulia Yu. Enakieva, Julien Michalak, Inna A. Abdulaeva, Marina V. Volostnykh, Christine Stern, et al.. General and Scalable Approach to A 2 B- and A 2 BC-Type Porphyrin Phosphonate Diesters. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2016, 2016 (28), pp.4881 - 4892. ⟨10.1002/ejoc.201600857⟩. ⟨hal-01429823⟩

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