Direct C–H azidation of calix[4]arene as a novel method to access meta substituted derivatives. Issue 39 (23rd September 2015)

• Record Type: Journal Article
• Authors: Stejskal, František; Eigner, Václav; Dvořáková, Hana; Cuřínová, Petra; Lhoták, Pavel
• Is Part Of: Tetrahedron letters. Volume 56:Issue 39(2015)
• Page Start: 5357
• Page End: 5361
• Publication Date: 2015-09-23
• Subjects: YDRMWZTYFKKFIT-UHFFFAOYSA-N -- CKOBMFCDPDBUTR-UHFFFAOYSA-N -- ZUSVSELXGVXORW-UHFFFAOYSA-N -- ZOISEUADUNZSDF-UHFFFAOYSA-N -- QYUOPPLURYIPSV-UHFFFAOYSA-N -- ZUAXNLMQHBURFY-UHFFFAOYSA-N -- XWHXECGFJOBOAM-UHFFFAOYSA-N; Calixarene -- Azidation -- Regioselectivity -- Click reaction -- X-ray structure -- Triazoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.08.002
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A novel method for the regioselective meta substitution of calix[4]arenes based on the direct C–H azidation of an amino-substituted calixarene immobilized in the cone conformation is described. Reaction with trimethylsilyl azide and tert -butyl hydroperoxide in the presence of CuBr as a catalyst, provided, depending on the stoichiometry, mono- or bis-azide-substituted derivatives in good yields under mild reaction conditions. meta -Azido calixarenes represent potentially valuable synthetic intermediates for the preparation of calixarenes possessing unusual substitution patterns as demonstrated by a click reaction with p -nitrophenyl acetylene.