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Functionalization at Will of Rim-Differentiated Pillar[5]arenes
[Image: see text] The development of an efficient synthetic route toward rim-differentiated C(5)-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scal...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6558637/ https://www.ncbi.nlm.nih.gov/pubmed/31002251 http://dx.doi.org/10.1021/acs.orglett.9b01123 |
Sumario: | [Image: see text] The development of an efficient synthetic route toward rim-differentiated C(5)-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C(5)-symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki–Miyaura coupling. Afterward, BBr(3) demethylation activates another rim for similar functionalizations. |
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