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- Title
Tetraalkylammonium Salts as Hydrogen‐Bonding Catalysts.
- Authors
Shirakawa, Seiji; Liu, Shiyao; Kaneko, Shiho; Kumatabara, Yusuke; Fukuda, Airi; Omagari, Yumi; Maruoka, Keiji
- Abstract
Although the hydrogen‐bonding ability of the α hydrogen atoms on tetraalkylammonium salts is often discussed with respect to phase‐transfer catalysts, catalysis that utilizes the hydrogen‐bond‐donor properties of tetraalkylammonium salts remains unknown. Herein, we demonstrate hydrogen‐bonding catalysis with newly designed tetraalkylammonium salt catalysts in Mannich‐type reactions. The structure and the hydrogen‐bonding ability of the new ammonium salts were investigated by X‐ray diffraction analysis and NMR titration studies.Cats with hitherto unknown talents: Tetraalkylammonium salts are widely used for phase‐transfer catalysis. It is now demonstrated that they can also function as hydrogen‐bonding catalysts. The hydrogen‐bonding ability of appropriately designed ammonium salt catalysts was evaluated in Mannich‐type reactions of N‐acyl isoquinolines and NMR titration studies. Structural information was obtained by X‐ray crystallography (see picture).
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 52, p15767
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201508659