Convenient Reductive Methylation of Amines with Carbonates at Room Temperature

Yuehui Li, Iván Sorribes, Cristian Vicent, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Methylation of amines is a fundamental and commonly used reaction in organic synthesis. Many methods are known including various reductive methylations using formaldehyde, formic acid, or carbon dioxide in the presence of reductants. However, several of these methods suffer from limited substrate scope and chemoselectivity because of the different nucleophilicities of substrates. In this respect, the combination of carbonates and hydrosilanes is a valuable methylation source in the presence of Pt-based catalysts. This highly tunable method allows for methylation of both aromatic and aliphatic amines, and chemoselective methylation of aminoalcohols and diamines. Notably, the in situ-formed catalyst can also be used for the reduction of carbonates to methanol at room temperature. Mechanistic insights on intermediates formed during the reaction pathway were obtained by using ESI mass spectrometry.

Original languageEnglish
Pages (from-to)16759-16763
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number47
DOIs
StatePublished - 1 Nov 2015
Externally publishedYes

Keywords

  • alkylation
  • carbonates
  • platinum
  • reduction
  • silanes

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