Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 3976-3980Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01123
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Funding
- 973 National Basic Research Program of China [2015CB856500]
- National Science Foundation of China [21871208]
- National Thousand Young Talents Program of China
- Tianjin City Thousand Talents Program
- 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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