title: C-C Bond Formation: Synthesis of C5 Substituted Pyrimidine and C8 Substituted Purine Nucleosides Using Water Soluble Pd-imidate Complex.
abstract: The synthesis of a highly efficient, water soluble [Pd(Sacc)2 (TPA)2 ] complex for C-C bond formation is described. Additionally, application of the [Pd(Sacc)2 (TPA)2 ] complex for Suzuki-Miyaura arylation of all four nucleosides (5-iodo-2'-deoxyuridine [5-IdU], 5-iodo-2'-deoxycytidine [5-IdC], 8-bromo-2'-deoxyadenosine, and 8-bromo-2'-deoxyguanosine) with various aryl/heteroaryl boronic acids in plain water under milder conditions is demonstrated. © 2016 by John Wiley & Sons, Inc.
authors.affiliation: Institute of Chemical Technology, Mumbai, India.
authors.forename: Vijay
authors.initials: V
authors.lastname: Gayakhe
authors.affiliation: Institute of Chemical Technology, Mumbai, India.
authors.forename: Ajaykumar V
authors.initials: AV
authors.lastname: Ardhapure
authors.affiliation: Institute of Chemical Technology, Mumbai, India.
authors.forename: Anant R
authors.initials: AR
authors.lastname: Kapdi
authors.affiliation: Rasayan, Encinitas, California.
authors.forename: Yogesh S
authors.initials: YS
authors.lastname: Sanghvi
authors.affiliation: Departamento de Ingeniería Minera, Geológica, y Cartográfica, Área de Química Inorgánica, Regional Campus of International Excellence "Campus Mare Nostrum," Universidad Politécnica de Cartagena, Cartagena, Spain.
authors.forename: Jose Luis
authors.initials: JL
authors.lastname: Serrano
authors.affiliation: Ernst-Moritz-Arndt-Universität Greifswald, Institut für Biochemie, Greifswald, Germany.
authors.forename: Carola
authors.initials: C
authors.lastname: Schulzke
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry; D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D014867:Water
chemical_list: C439365:8-bromo-2'-deoxyguanosine; D003839:Deoxyadenosines; D009943:Organophosphorus Compounds; D011684:Purine Nucleosides; D011743:Pyrimidines; C434331:phosphoramidite; D014867:Water; C042464:8-bromo-2'-deoxyadenosine; D010165:Palladium; D003849:Deoxyguanosine
keywords: Suzuki-Miyaura cross-coupling; base-modified nucleosides; nucleotides; palladium catalyst