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.

 

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

Vijay Gayakhe^†, Ajaykumar Ardhapure^†, Anant R. Kapdi^*†, Yogesh S. Sanghvi^‡, Jose Luis Serrano^§, Luis García^§, Jose Pérez^§, Joaquím García^∥, Gregorio Sánchez^∥, Christian Fischer^⊥, and Carola Schulzke^⊥

^† Institute of Chemical Technology, Mumbai Nathalal Road, Matunga, Mumbai 400019, India

^‡ Rasayan, Inc. 2802 Crystal Ridge Road, Encinitas, California 92024-6615, United States

^§ Departamento de Ingeniería Minera, Geológica y Cartográfica, Universidad Politécnica de Cartagena, Área de Química Inorgánica, Regional Campus of International Excellence “Campus Mare Nostrum”, Universidad Politécnica de Cartagena, 30203 Cartagena, Spain

^∥ Departamento de Química Inorgánica, Regional Campus of International Excellence “Campus Mare Nostrum”, Universidad de Murcia, 30071 Murcia, Spain

^⊥ Ernst-Moritz-Arndt-Universität Greifswald, Institut für Biochemie, Felix-Hausdorff-Strasse 4, 17489 Greifswald, Germany

J. Org. Chem., Article ASAP

DOI: 10.1021/acs.joc.5b02475

Publication Date (Web): February 27, 2016

Copyright © 2016 American Chemical Society

*E-mail: ar.kapdi@ictmumbai.edu.in.

 http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02475

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