Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes.

A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.

Crystal structure of 5-(dibenzo-furan-4-yl)-2'-deoxy-uridine.

The mol-ecule of the title compound, CHNO, has a bent rather than a linear conformation supported by three intra-molecular C-H⋯O hydrogen bonds. The packing in the crystal lattice is largely determined by inter-actions between hydrogen atoms with oxygen atom lone pairs with one mol-ecule inter-acting with neigbouring mol-ecules O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. The title compound crystallizes in the chiral ortho-rhom-bic space group 222.

C-C Bond Formation: Synthesis of C5 Substituted Pyrimidine and C8 Substituted Purine Nucleosides Using Water Soluble Pd-imidate Complex.

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.

Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling.

A broadly applicable catalyst system consisting of water-soluble Pd--imidate complexes has been enployed for the Suzuki-Miyaura cross-coupling of four different nucleosides in water under mild conditions. The efficient nature of the catalyst system also allowed its application in developing a microwave-assisted protocol with the purpose of expediting the catalytic reaction. Preliminary mechanistic studies, assisted by catalyst poison tests and stoichiometric tests performed using an electrospray ionization spectrometer, revealed the possible presence of a homotopic catalyst system.

Catalytic C-H bond functionalisation of purine and pyrimidine nucleosides: a synthetic and mechanistic perspective.

C-H bond functionalisation of heteroarenes, especially nucleosides, has received a lot of attention in the past few years. This review describes the state-of the art in this area with a global aspiration for possibly functionalising purine and pyrimidine moieties in more complex biomolecular systems, such as DNA/RNA in the near future.'