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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...

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Detalles Bibliográficos
Autores principales: Demay-Drouhard, Paul, Du, Ke, Samanta, Kushal, Wan, Xintong, Yang, Weiwei, Srinivasan, Rajavel, Sue, Andrew C.-H., Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
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
Descripción
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.