Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed C[BOND]H Bond Activation

Authors

  • Prof. Mahesh K. Lakshman,

    Corresponding author
    1. Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
    • Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
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  • Dr. Ashoke C. Deb,

    1. Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
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  • Dr. Raghu Ram Chamala,

    1. Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
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  • Dr. Padmanava Pradhan,

    1. Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
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  • Dr. Ramendra Pratap

    1. Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198 (USA)
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  • This work was partially supported by a PSC CUNY award to M.K.L. Infrastructural support at CCNY was provided by the NIH RCMI Grant G12 RR03060. We thank Ona Liu (undergraduate research participant) for her contribution to this work, Frontier Scientific for generous samples of arylboronic acids, and Dr. Bill Boggess and Nonka Sevova (University of Notre Dame) for HRMS analyses (NSF Grant CHE-0741793).

Abstract

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One aryl or two? The title reaction predominantly gives the monoarylation products with various amounts of diarylation product being observed in almost all cases (see scheme). Aryl iodides as well as aryl bromides were reactive under the optimized reaction conditions. The multiple nitrogen atoms in the purine, and oxygen atoms in the saccharide posed no problems in these transformations.

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