Catalytic Oxidative Deamination by Water with H2Liberation

Shan Tang, Michael Rauch, Michael Montag, Yael Diskin-Posner, Yehoshoa Ben-David, David Milstein

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Selective oxidative deamination has long been considered to be an important but challenging transformation, although it is a common critical process in the metabolism of bioactive amino compounds. Most of the synthetic methods developed so far rely on the use of stoichiometric amounts of strong and toxic oxidants. Here we present a green and efficient method for oxidative deamination, using water as the oxidant, catalyzed by a ruthenium pincer complex. This unprecedented reaction protocol liberates hydrogen gas and avoids the use of sacrificial oxidants. A wide variety of primary amines are selectively transformed to carboxylates or ketones in good to high yields. It is noteworthy that mechanistic experiments and DFT calculations indicate that in addition to serving as the oxidant, water also plays an important role in assisting the hydrogen liberation steps involved in amine dehydrogenation.

Original languageEnglish
Pages (from-to)20875-20882
Number of pages8
JournalJournal of the American Chemical Society
Volume142
Issue number49
DOIs
Publication statusPublished - Dec 9 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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