What is Borrowing Hydrogen Catalysis?

  • Author: ChemistryViews.org
  • Published Date: 04 October 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: What is Borrowing Hydrogen Catalysis?

Borrowing hydrogen catalysis, also called hydrogen autotransfer or dehydrogenative activation, is a method in organic chemistry to activate, for example, alcohols. Alcohols are not very reactive, in contrast to their oxidation products, aldehydes and ketones.

These carbonyl compounds, which technically differ from the alcohols by one H2 molecule, are much better electrophiles and can be used in a variety of reactions. Borrowing hydrogen catalysis uses this "chemical detour" as method of activation.

Example Reaction

  1. A catalyst "borrows" H2 from an alcohol, forming a carbonyl compound.
  2. The carbonyl compound takes part in a reaction which would not be possible for the alcohol.
  3. The catalyst "returns" the hydrogen to the reaction product afterward.

The overall process allows alcohols to be converted into amines, to form C–C bonds, or to be functionalized at the β-position. The catalysts are usually transition metal complexes, e.g., Ru, Ir, or Rh compounds. In addition to alcohols, borrowing hydrogen catalysis can also be applied to amines and even alkanes.



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Article Information

DOI: 10.1002/chemv.201600081


Article Views: 3210

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