Direct C–H Azidation of Calix[4]arene as a Novel Method to Access Meta Substituted Derivatives

0446682 - ÚCHP 2016 RIV GB eng J - Journal Article
Stejskal, F. - Eigner, V. - Dvořáková, H. - Cuřínová, Petra - Lhoták, P.
Direct C–H Azidation of Calix[4]arene as a Novel Method to Access Meta Substituted Derivatives.
Tetrahedron Letters. Roč. 56, č. 39 (2015), s. 5357-5361. ISSN 0040-4039. E-ISSN 1873-3581
Institutional support: RVO:67985858
Keywords : calixarene * azidation * regionselectivity
Subject RIV: CC - Organic Chemistry
Impact factor: 2.347, year: 2015

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.
Permanent Link: http://hdl.handle.net/11104/0250260