Direct Synthesis of Amides by Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and Ammonia Catalyzed by a Manganese Pincer Complex: Unexpected Crucial Role of Base

Prosenjit Daw, Amit Kumar, Noel Angel Espinosa-Jalapa, Yehoshoa Ben-David, David Milstein*

*Corresponding author for this work

    Research output: Contribution to journalLetterpeer-review

    69 Citations (Scopus)
    101 Downloads (Pure)

    Abstract

    Amide synthesis is one of the most important transformations in chemistry and biology. The direct use of ammonia for the incorporation of nitrogen functionalities in organic molecules is an attractive and environmentally benign method. We present here a new synthesis of amides by acceptorless dehydrogenative coupling of benzyl alcohols and ammonia. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of a stoichiometric base, making the overall process economical, efficient, and sustainable. Interesting mechanistic insights based on detailed experimental observations, indicating the crucial role of the base, are provided.

    Original languageEnglish
    Pages (from-to)12202-12206
    Number of pages5
    JournalJournal of the American Chemical Society
    Volume141
    Issue number31
    Early online date15 Jul 2019
    DOIs
    Publication statusPublished - 7 Aug 2019

    Funding

    This research was supported by the European Research Council (ERC AdG 692775). D.M. holds the Israel Matz Professorial Chair of Organic Chemistry. P.D. and A.K. thank the Planning and Budgeting Committee (PBC) for a postdoctoral fellowship. P.D. also thanks the Weizmann Institute of Science and Koshland Foundation for a senior postdoctoral fellowship. N.A.E.-J. thanks Mr. Armando Jinich for a postdoctoral fellowship.

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • General Chemistry
    • Biochemistry
    • Colloid and Surface Chemistry

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