16. Lewis Acids

  1. Peter I. Dalko
  1. Tatjana Heckel and
  2. René Wilhelm

Published Online: 23 AUG 2013

DOI: 10.1002/9783527658862.ch16

Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

How to Cite

Heckel, T. and Wilhelm, R. (2013) Lewis Acids, in Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications (ed P. I. Dalko), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527658862.ch16

Editor Information

  1. Université Paris-Descartes, PRES Sorbonne Paris Cité, CNRS, 45, rue des Saints-Pères, 75270 Paris Cedex 06, France

Publication History

  1. Published Online: 23 AUG 2013
  2. Published Print: 23 OCT 2013

ISBN Information

Print ISBN: 9783527332366

Online ISBN: 9783527658862

SEARCH

Keywords:

  • Lewis acids;
  • non-covalent activations;
  • organocatalysis

Summary

This chapter gives a brief overview of Lewis acids as organocatalysts. Lewis acids are among the most applied catalysts in organic chemistry. Many reactions are accelerated with metal salts like aluminum chloride, titanium chloride, zinc chloride and so on. Asymmetric catalysis can be performed with these metal salts by the addition of enantiopure ligands. However, it is often not realized that not only metal or boron centers can function as Lewis acids. Carbenium, silyl, or phosphonium cations can also exhibit Lewis acid catalytic activity. Furthermore, hypervalent compounds based on phosphorus and silicon have inherent Lewis acidity. In addition, organic salts with a melting point below 100 °C, ionic liquids, can due to their cations be Lewis acidic and can catalyze reactions either in stoichiometric or substoichiometric amounts. This chapter gives an overview of the known classes of metal-free Lewis acids and their application in catalysis.