Pd-Catalyzed Amination of Nucleoside Arylsulfonates to yield N6-Aryl-2,6-Diaminopurine Nucleosides†
Padmaja Gunda
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, NY 10031, USA, Fax: (+1) 212-650-6107
Search for more papers by this authorLarry M. Russon Dr.
Analytica of Branford Inc. 29 Business Park Drive, Branford, CT 06405, USA
Search for more papers by this authorMahesh K. Lakshman Prof.
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, NY 10031, USA, Fax: (+1) 212-650-6107
Search for more papers by this authorPadmaja Gunda
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, NY 10031, USA, Fax: (+1) 212-650-6107
Search for more papers by this authorLarry M. Russon Dr.
Analytica of Branford Inc. 29 Business Park Drive, Branford, CT 06405, USA
Search for more papers by this authorMahesh K. Lakshman Prof.
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, NY 10031, USA, Fax: (+1) 212-650-6107
Search for more papers by this authorThis work was supported by NSF grant CHE-0314326 and a PSC-CUNY 35 award. Acquisition of a 500 MHz NMR spectrometer was funded by NSF grant CHE-0210295. Professor S. L. Buchwald (MIT) is thanked for a sample of L 5, and Dr. G. Li (CombiPhos Catalysts Inc.) is thanked for samples of L 6 and L 7.
Graphical Abstract
Substituents on both the nucleoside arylsulfonate as well as the aryl amine component have a significant impact on their coupling to form 2,6-diaminopurine-2′-deoxyribonucleosides (see scheme). A systematic study of ligands for the Pd catalysts in amination and CC cross-coupling reactions gives insight into the structural elements that lead to effective catalysis.
Supporting Information
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