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

Paul DemayDrouhard | Zendy; Ke Du | Zendy; Kushal Samanta | Zendy; Xintong Wan | Zendy; Weiwei Yang | Zendy; Rajavel Srinivasan | Zendy; Andrew C.H. Sue | Zendy; Han Zuilhof | Zendy

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

Author(s) -

Paul DemayDrouhard,

Ke Du,

Kushal Samanta,

Xintong Wan,

Weiwei Yang,

Rajavel Srinivasan,

Andrew C.H. Sue,

Han Zuilhof

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b01123

Subject(s) - chemistry , demethylation , pillar , surface modification , combinatorial chemistry , sulfur , fluoride , organic chemistry , inorganic chemistry , biochemistry , gene expression , structural engineering , engineering , dna methylation , gene

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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