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      3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer

      1 , 1
      Chemical Reviews
      American Chemical Society (ACS)

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          Abstract

          The conservation of our element resources is a fundamental challenge of mankind. The development of alcohol refunctionalization reactions is a possible fossil carbon conservation strategy since alcohols can be obtained from indigestible and abundantly available biomass. The conservation of our rare noble metals, frequently used in key technologies such as catalysis, might be feasible by replacing them with highly abundant metals. The alkylation of amines by alcohols and related C-C coupling reactions are early examples of alcohol refunctionalization reactions. These reactions follow mostly the borrowing hydrogen or hydrogen autotransfer catalysis concept, and many 3d-metal catalysts have been disclosed in recent years. In this review, we summarize the progress made in developing Cu, Ni, Co, Fe, and Mn catalysts for C-N and C-C bond formation reactions with alcohols and amines using the borrowing hydrogen or hydrogen autotransfer concept. We expect that the findings in this field will inspire others to develop new efficient and selective earth-abundant metal catalysts for borrowing hydrogen or hydrogen autotransfer applications or to develop novel alcohol refunctionalization reactions that can be mediated by such metals.

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          Author and article information

          Journal
          Chemical Reviews
          Chem. Rev.
          American Chemical Society (ACS)
          0009-2665
          1520-6890
          November 20 2018
          November 20 2018
          Affiliations
          [1 ]Inorganic Chemistry II − Catalyst Design, University of Bayreuth, 95440 Bayreuth, Germany
          Article
          10.1021/acs.chemrev.8b00306
          30457320
          c4fa72cb-bbbb-4041-9328-1180db6cdb7c
          © 2018
          History

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