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

SYSNO ASEP	0446682
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Direct C–H Azidation of Calix[4]arene as a Novel Method to Access Meta Substituted Derivatives
Author(s)	Stejskal, F. (CZ) Eigner, V. (CZ) Dvořáková, H. (CZ) Cuřínová, Petra (UCHP-M)_{RID, SAI, ORCID} Lhoták, P. (CZ)
Source Title	Tetrahedron Letters. - : Elsevier - ISSN 0040-4039 Roč. 56, č. 39 (2015), s. 5357-5361
Number of pages	5 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	calixarene ; azidation ; regionselectivity
Subject RIV	CC - Organic Chemistry
Institutional support	UCHP-M - RVO:67985858
UT WOS	000361252200011
EID SCOPUS	84939654736
DOI	10.1016/j.tetlet.2015.08.002
Annotation	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.
Workplace	Institute of Chemical Process Fundamentals
Contact	Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227
Year of Publishing	2016

Number of the records: 1