Convergent Ditopic Receptors Enhance Anion Binding upon Alkali Metal Complexation for Catalyzing the Ritter Reaction
- 14 January 2019
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 21 (3) , 652-655
Abstract
A supramolecular approach to catalyzing the Ritter reaction by utilizing enhanced anion-binding affinity in the presence of alkali metal cations was developed with ditopic hydrogen-bonded amide macrocycles. With prebound cations in the macrocycle, particularly Li+ ion, their metal complexes exhibit greatly enhanced catalytic activities. The catalysis is switchable by removal or addition of the bound cation. The method described in this work may be generalized for use in other anion-triggered organic reactions involving heteroditopic receptors capable of ion pairing.Keywords
Funding Information
- National Natural Science Foundation of China (21572143)
- National Institute of General Medical Sciences (R01-GM087398)
- National Science Foundation
- Post-Doctoral Research and Development Foundation, Sichuan University (2017SCU12001)
- State Key Laboratory of Supramolecular Structure and Materials, jilin University (SKLSSM201831)
This publication has 65 references indexed in Scilit:
- A macrocyclic aromatic pyridone pentamer as a highly efficient organocatalyst for the direct arylations of unactivated arenesChemical Communications, 2013
- Aromatic Amide Foldamers: Structures, Properties, and FunctionsChemical Reviews, 2012
- Turn-On Fluorescent Sensor for Selective Detection of Zn2+, Cd2+, and Hg2+ in WaterThe Journal of Organic Chemistry, 2012
- Lithium cation enhances anion binding in a tripodal phosphine oxide-based ditopic receptorChemical Communications, 2011
- Environmentally Responsive Threading, Dethreading, and Fixation of Anion-Induced PseudorotaxanesJournal of the American Chemical Society, 2011
- Ion pair receptorsChemical Society Reviews, 2010
- Hollow Crescents, Helices, and Macrocycles from Enforced Folding and Folding-Assisted MacrocyclizationAccounts of Chemical Research, 2008
- Macrocyclic and Helical Oligoamides as a New Class of G-Quadruplex LigandsJournal of the American Chemical Society, 2007
- Stepwise and Dramatic Enhancement of Anion Recognition with a Triple-Site Receptor Based on the Calix[4]arene Framework Using Two Different Cationic EffectorsJournal of the American Chemical Society, 2005
- Synthesis and properties of new calixarene-based ditopic receptors for the simultaneous complexation of cations and carboxylate anionsJournal of the Chemical Society, Perkin Transactions 2, 1998