|Title||Functionalization at Will of Rim-Differentiated Pillararenes|
|Author(s)||Demay-Drouhard, Paul; Du, Ke; Samanta, Kushal; Wan, Xintong; Yang, Weiwei; Srinivasan, Rajavel; Sue, Andrew C.H.; Zuilhof, Han|
|Source||Organic Letters 21 (2019)11. - ISSN 1523-7060 - p. 3976 - 3980.|
|Publication type||Refereed Article in a scientific journal|
The development of an efficient synthetic route toward rim-differentiated C 5 -symmetric pillararenes (Ps), 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 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.