Issue 14, 2017

Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C–N bond formation, no metal needed

Abstract

The reaction of a variety of N6-aryl 2′-deoxyadenosine and adenosine derivatives with PhI(OAc)2 in 1,1,1,3,3,3-hexafluoro-2-propanol provides a facile access to benzimidazopurine nucleoside analogues by metal-free C–N bond formation with a purinyl nitrogen atom. These reactions likely proceed via radical-cation/radical processes as indicated by radical inhibition experiments.

Graphical abstract: Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C–N bond formation, no metal needed

Supplementary files

Article information

Article type
Communication
Submitted
22 Sep 2016
Accepted
28 Nov 2016
First published
15 Dec 2016

Chem. Commun., 2017,53, 2226-2229

Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C–N bond formation, no metal needed

S. Satishkumar and M. K. Lakshman, Chem. Commun., 2017, 53, 2226 DOI: 10.1039/C6CC07722F

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