Ruthenium-catalyzed synthesis of secondary alkylamines: Selective alkylation with aliphatic amines

Sebastian Bähn, Dirk Hollmann, Annegret Tillack, Matthias Bellera

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

The chemoselective N-alkylation of tert-alkylamines applying aliphatic amines is described for the first time. In the presence of the Shvo catalyst 1, tert-octylamine 4 and 1-adamantylamine 5 are alkylated using primary, secondary, and even tertiary amines to give the corresponding monoalkylated tert-alkylamine in moderate to very good yields and excellent selectivity. This novel reaction proceeds without an additional hydrogen source and ammonia is formed as the only by-product.

Original languageEnglish
Pages (from-to)2099-2103
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number13
DOIs
StatePublished - 5 Sep 2008
Externally publishedYes

Keywords

  • Alkylation
  • Amines
  • Homogeneous catalysis
  • Hydrogen transfer
  • Ruthenium

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