Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence

Miguel Peña-Lõpez, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

Abstract

The synthesis of lactones and lactams by using iron(II) pincer-catalyzed dehydrogenative methodology was developed. Starting from 1,n-diols or 1,n-amino alcohols, this domino transformation takes place through initial dehydrogenation of the substrates, subsequent intramolecular cyclization, and final oxidation to afford the desired products in good yields. The ability to access heterocycles of different sizes makes this protocol especially versatile, in which two consecutive oxidation reactions are performed without requiring an external oxidant. In this paper, we report the application of the Fe-MACHO-BH complex [carbonylhydrido(tetrahydroborato)[bis(2-diisopropylphosphinoethyl)amino]iron(II)] in this atom-efficient and environmentally benign process, for which molecular hydrogen is formed as the only stoichiometric side product. Just a little pinch: The iron(II) pincer-catalyzed synthesis of lactones and lactams from easily available 1,n-diols and 1,n-amino alcohols is explored. The use of a nontoxic metal as well as the generation of molecular hydrogen as the only stoichiometric byproduct makes this method a highly atom-efficient and environmentally benign process.

Original languageEnglish
Pages (from-to)865-871
Number of pages7
JournalChemCatChem
Volume7
Issue number5
DOIs
StatePublished - Mar 2015
Externally publishedYes

Keywords

  • dehydrogenative oxidation
  • iron
  • lactams
  • lactones
  • pincer complexes

Fingerprint

Dive into the research topics of 'Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence'. Together they form a unique fingerprint.

Cite this