4.8 Article

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

Journal

ORGANIC LETTERS
Volume 21, Issue 11, Pages 3976-3980

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01123

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Funding

  1. 973 National Basic Research Program of China [2015CB856500]
  2. National Science Foundation of China [21871208]
  3. National Thousand Young Talents Program of China
  4. Tianjin City Thousand Talents Program
  5. Wageningen University

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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-iyaura coupling. Afterward, BBr3 demethylation activates another rim for similar functionalizations.

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