Unknown

Dataset Information

0

Functionalization at Will of Rim-Differentiated Pillar[5]arenes.

ABSTRACT: The development of an efficient synthetic route toward rim-differentiated C5-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 C5-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, BBr3 demethylation activates another rim for similar functionalizations.

SUBMITTER: Demay-Drouhard P 

PROVIDER: S-EPMC6558637 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Functionalization at Will of Rim-Differentiated Pillar[5]arenes.

Demay-Drouhard Paul P   Du Ke K   Samanta Kushal K   Wan Xintong X   Yang Weiwei W   Srinivasan Rajavel R   Sue Andrew C-H AC   Zuilhof Han H  

Organic letters 20190419 11

The development of an efficient synthetic route toward rim-differentiated C<sub>5</sub>-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<sub>5</sub>-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) re  ...[more]

Similar Datasets

Unknown Rim-Differentiated C<sub>5</sub>-Symmetric Tiara-Pillar[5]arenes.
| S-EPMC5765533 | biostudies-literature
Unknown Stereochemical Inversion of Rim-Differentiated Pillar[5]arene Molecular Swings.
| S-EPMC7498154 | biostudies-literature
Unknown Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes.
| S-EPMC6036973 | biostudies-literature
Unknown Double heteroatom functionalization of arenes using benzyne three-component coupling.
| S-EPMC4832838 | biostudies-other
Unknown per-Alkoxy-pillar[5]arenes as Electron Donors: Electrochemical Properties of Dimethoxy-Pillar[5]arene and Its Corresponding Rotaxane.
| S-EPMC7180461 | biostudies-literature
Unknown On the Stability and Formation of Pillar[n]arenes: a DFT Study.
| S-EPMC8576824 | biostudies-literature
Unknown Organization of lower rim O-alkylated p-phosphonic acid calix[4]arenes.
| S-EPMC2723774 | biostudies-literature
Unknown Ligand-accelerated non-directed C-H functionalization of arenes.
| S-EPMC5726549 | biostudies-literature
Unknown Dynamics in Flexible Pillar[<i>n</i>]arenes Probed by Solid-State NMR.
| S-EPMC8237263 | biostudies-literature
Unknown Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions.
| S-EPMC8777861 | biostudies-literature