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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
This work was supported by the Natural Science Foundation of China (21772098, 21390400, 21602116), and Tsinghua University Initiative Scientific Research Program (20131080083, 20141081295).Further Information
Publication History
Received: 23 May 2019
Accepted after revision: 26 June 2019
Publication Date:
10 July 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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