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

Paul Demay-Drouhard, Ke Du, Kushal Samanta, Xintong Wan, Weiwei Yang, Rajavel Srinivasan, Andrew C.H. Sue, Han Zuilhof*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3976-3980
JournalOrganic Letters
Volume21
Issue number11
DOIs
Publication statusPublished - 19 Apr 2019

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Demay-Drouhard, P., Du, K., Samanta, K., Wan, X., Yang, W., Srinivasan, R., ... Zuilhof, H. (2019). Functionalization at Will of Rim-Differentiated Pillar[5]arenes. Organic Letters, 21(11), 3976-3980. https://doi.org/10.1021/acs.orglett.9b01123