Synthesis and structural aspects of N-triflylphosphoramides and their calcium salts'highly acidic and effective Brønsted acids

Magnus Rueping*, Boris J. Nachtsheim, René M. Koenigs, Winai Ieawsuwan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

80 Scopus citations

Abstract

Recently, 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides emerged as a new class of potent Brønsted acid catalysts. In this paper we describe the efficient synthesis of various BINOL-based N- triflylphosphoramides and their calcium salts. Furthermore, X-ray crystal structure analysis combined with energy-dispersive X-ray spectroscopy (EDX) measurements confirmed that the synthesised chiral N-triflylphosphoramides are highly acidic metal-free catalysts. Freedom! The synthesis and structure determination of various 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides and their corresponding calcium salts is presented. A simple acidic treatment of the calcium salts provides the metal-free Brønsted acids (see scheme; Tf=trifluoromethanesulfonyl).

Original languageEnglish (US)
Pages (from-to)13116-13126
Number of pages11
JournalChemistry - A European Journal
Volume16
Issue number44
DOIs
StatePublished - Nov 22 2010

Keywords

  • Brønsted acids
  • asymmetric synthesis
  • calcium
  • homogeneous catalysis
  • reaction mechanisms

ASJC Scopus subject areas

  • Chemistry(all)

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