Synthesis of binaphthyl based phosphine and phosphite ligands

Chem Soc Rev. 2013 Aug 21;42(16):6990-7027. doi: 10.1039/c3cs60116a.

Abstract

The development of large scale synthesis of enantiopure and thermally stable (R)- and (S)-BINOL molecules constitutes a key milestone in the field of asymmetric catalysis. Particularly, a great variety of chiral binaphthyl-based phosphorus compounds, herein represented by phosphite and phosphine classes, have earned considerable relevance due to their versatility as ligands in enantioselective metal-catalysed reactions, allowing the preparation of optically active products with the desired enantiopurity. This review highlights the most relevant concepts and accounts regarding general synthetic procedures for binaphthyl-based mono- and bidentate phosphites and phosphines. Furthermore, the search for environmentally benign chemical catalytic processes compelled us to also give special attention to the functionalisation of binaphthyl-based phosphorus ligands for use in alternative reaction media. When available, a critical selection of their applications in catalysis is briefly assessed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Ligands
  • Naphthols / chemistry*
  • Phosphines / chemical synthesis
  • Phosphines / chemistry*
  • Phosphites / chemical synthesis
  • Phosphites / chemistry*

Substances

  • BINOL, naphthol
  • Ligands
  • Naphthols
  • Phosphines
  • Phosphites
  • phosphine