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Synthesis 2013; 45(6): 777-784
DOI: 10.1055/s-0032-1318307
DOI: 10.1055/s-0032-1318307
paper
N-Arylation of Protected Azamacrocycles
Further Information
Publication History
Received: 27 December 2012
Accepted after revision: 02 February 2013
Publication Date:
18 February 2013 (online)
Abstract
A rapid method for efficient palladium-catalyzed N-arylation of polynitrogenated macrocycles is presented. Its applicability for functionalization of protected azamacrocycles of various sizes with substituted aryl bromides of optional electronic properties is demonstrated. The compatibility of the protocol with common N-protecting schemes as well as the impact of electronic versus steric factors is discussed. Using a commercially available catalytic system and easily available alkoxide or phenoxide base, the method provides moderate to excellent yields of N-arylated azamacrocycles (45–96%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are 1H and 13C NMR spectra.
- Supporting Information
-
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