Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 550673
Title Functionalization at Will of Rim-Differentiated Pillar[5]arenes
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.
Department(s) Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2019

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.

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