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Apical Functionalization of Tribenzotriquinacenes
Author(s) -
Dhara Ayan,
Weinmann Joshua,
Krause AnaMaria,
Beuerle Florian
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602622
Subject(s) - sonogashira coupling , alkyne , moiety , surface modification , cycloaddition , chemistry , azide , derivatization , demethylation , combinatorial chemistry , stereochemistry , organic chemistry , palladium , biochemistry , gene expression , high performance liquid chromatography , dna methylation , gene , catalysis
The introduction of one alkyne moiety at the central carbon atom of the tripodal tribenzotriquinacene scaffold allows easy access to a great variety of apically functionalized derivatives. The spatially well‐separated arrangement of different functional units on the convex face and outer rim was further proven by single‐crystal X‐ray studies. Subsequent modifications that feature a general protecting group‐free strategy for the demethylation of protected catechols in the presence of a terminal alkyne group, an azide–alkyne Huisgen cycloaddition, and Sonogashira cross‐coupling reactions showcase the high synthetic potential of this modular approach for tribenzotriquinacene derivatization.