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Synlett 2019; 30(17): 1940-1949
DOI: 10.1055/s-0037-1611890
DOI: 10.1055/s-0037-1611890
account
Recent Progress in Equilibrium Acidity Studies of Organocatalysts
Autor*innen
This work was supported by the Natural Science Foundation of China (21772098, 21390400, 21602116), and Tsinghua University Initiative Scientific Research Program (20131080083, 20141081295).
Weitere Informationen
Publikationsverlauf
Received: 23. Mai 2019
Accepted after revision: 26. Juni 2019
Publikationsdatum:
10. Juli 2019 (online)
Dedicated to the 100th anniversary of Nankai University
Abstract
This account summarizes our recent work on the pK a scales of some frequently used organocatalysts, especially those of hydrogen-bond-donor catalysts and stronger Brønsted acid catalysts. Most of these pK a values were obtained by the Bordwell overlapping indicator method, which is known to provide high accuracy. Linear free-energy relationships associated with pK a values are discussed in relation to understanding of reaction mechanisms.
1 Introduction
2 Single Hydrogen-Bonding Donors
2.1 Proline-Type Organocatalysts
2.2 Cinchona Alkaloids Bearing a Hydrogen-Bonding Donor in the 6′-Position
3 Double-Hydrogen-Bonding Donors
3.1 Thioureas
3.2 Squaramides
3.3 BINOLs
4 Stronger Brønsted Acids
5 N-Heterocyclic Carbenes
6 Summary and Outlook
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