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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.

SUBMITTER: Satishkumar S

PROVIDER: S-EPMC5309161 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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

Satishkumar Sakilam S Lakshman Mahesh K MK

Chemical communications (Cambridge, England) 20170201 14

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. ...[more]

PMID: 27976760

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