Get access

On the Acidity and Reactivity of Highly Effective Chiral Brønsted Acid Catalysts: Establishment of an Acidity Scale

Authors

  • Karl Kaupmees,

    1. Institute of Chemistry, University of Tartu, 14a Ravila Street, 50411 Tartu (Estonia)
    Search for more papers by this author
  • Nikita Tolstoluzhsky,

    1. RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, 52074 Aachen (Germany)
    Search for more papers by this author
  • Dr. Sadiya Raja,

    1. RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, 52074 Aachen (Germany)
    Search for more papers by this author
  • Prof. Dr. Magnus Rueping,

    Corresponding author
    1. RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, 52074 Aachen (Germany)
    • Magnus Rueping, RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, 52074 Aachen (Germany)

      Ivo Leito, Institute of Chemistry, University of Tartu, 14a Ravila Street, 50411 Tartu (Estonia)

    Search for more papers by this author
  • Prof. Dr. Ivo Leito

    Corresponding author
    1. Institute of Chemistry, University of Tartu, 14a Ravila Street, 50411 Tartu (Estonia)
    • Magnus Rueping, RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, 52074 Aachen (Germany)

      Ivo Leito, Institute of Chemistry, University of Tartu, 14a Ravila Street, 50411 Tartu (Estonia)

    Search for more papers by this author

  • Financial support by the DFG is gratefully acknowledged. The research of K.K. and I.L. was supported by Grant 9105 from the Estonian Science Foundation. We thank Prof. A. C. O’Donoghue for helpful discussions.

Abstract

original image

Stronger acid, higher speed: The pKa values of a range of binol-derived Brønsted acids of three different types were measured and found to correlate directly with the catalytic properties of the acids: higher rate constants kI were observed for more acidic Brønsted acid catalysts (see plot; binol=1,1′-bi-2-naphthol).

Get access to the full text of this article

Ancillary