Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols

Thomas L. Gianetti, Samuel P. Annen, Gustavo Santiso-Quinones, Markus Reiher, Matthias Driess, Hansjörg Grützmacher

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

The oxidation of alcohols with N2O as the hydrogen acceptor was achieved with low catalyst loadings of a rhodium complex that features a cooperative bis(olefin)amido ligand under mild conditions. Two different methods enable the formation of either the corresponding carboxylic acid or the ester. N2 and water are the only by-products. Mechanistic studies supported by DFT calculations suggest that the oxygen atom of N2O is transferred to the metal center by insertion into the Rh-H bond of a rhodium amino hydride species, generating a rhodium hydroxy complex as a key intermediate.

Original languageEnglish (US)
Pages (from-to)1854-1858
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number5
DOIs
StatePublished - Jan 26 2016
Externally publishedYes

Keywords

  • alcohols
  • catalysis
  • coupling reactions
  • dehydrogenation
  • nitrous oxide
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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