title: 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)2in 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.
authors.affiliation: Department of Chemistry and Biochemistry, The City College of New York, 160 Convent Avenue, New York, NY 10031, USA. mlakshman@ccny.cuny.edu.
authors.forename: Sakilam
authors.identifier: http://orcid.org/0000-0001-5557-3242
authors.initials: S
authors.lastname: Satishkumar
authors.affiliation: Department of Chemistry and Biochemistry, The City College of New York, 160 Convent Avenue, New York, NY 10031, USA. mlakshman@ccny.cuny.edu and The Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, NY 10016, USA.
authors.forename: Mahesh K
authors.identifier: http://orcid.org/0000-0002-9555-027X
authors.initials: MK
authors.lastname: Lakshman
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives*; D001562:Benzimidazoles / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003839:Deoxyadenosines / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008163:Luminescent Measurements; D009584:Nitrogen / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated
chemical_list: D000241:Adenosine; D001562:Benzimidazoles; D002244:Carbon; D003839:Deoxyadenosines; D005609:Free Radicals; D009584:Nitrogen; D009705:Nucleosides; D020005:Propanols; C001337:hexafluoroisopropanol; D006845:Hydrocarbons, Fluorinated; C031000:benzimidazole; C058118:2'-deoxyadenosine