Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

Research output: Contribution to journalJournal articleResearchpeer-review

  • Veronica Airoldi
  • Oreste Piccolo
  • Gabriella Roda
  • Rebecca Appiani
  • Bavo, Francesco
  • Riccardo Tassini
  • Stefano Paganelli
  • Sebastiano Arnoldi
  • Marco Pallavicini
  • Cristiano Bolchi

A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number2
Pages (from-to)162-168
Number of pages7
ISSN1434-193X
DOIs
Publication statusPublished - 16 Jan 2020
Externally publishedYes

    Research areas

  • Amination, Aquivion, Chemoselectivity, Cinacalcet, Sodium borohydride

ID: 259878939