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

• DOI: 10.1021/acs.joc.5b02475
• Publication Date: 2016-02-27T16:21:19Z
• Authors: Vijay Gayakhe; Ajaykumar Ardhapure; Anant R. Kapdi; Yogesh S. Sanghvi; Jose Luis Serrano; Luis García; Jose Pérez; Joaquím García; Gregorio Sánchez; Christian Fischer; Carola Schulzke
• Keywords: 01 natural sciences; 0104 chemical sciences

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.