As interdisciplinary integration of supramolecular chemistry and catalysis, supramolecular catalysis has paved a way for boosting highly efficient and selective transformation. With enzyme-mimetic pocket and specific recognition ability, macrocyclic compounds have shown great potential in this aspect. While the binding and activation in current systems is mainly driven by cation-relevant interactions or hydrophobic effects, the recent development of anion supramolecular chemistry has stimulated us to exploit an alternative, anion-recognition directed strategy. We propose that by taking advantages of the rich variety, geometry and interaction sites of anions, sophisticated cooperation and regulation of multiple noncovalent interactions can be manipulated for directing efficient and selective catalysis. In this talk, I will first present our progress on developing macrocycle-enabled counteranion trapping catalysis. Through tight trapping of the counteranion of an acid catalyst by tailored-made hydrogen-bonding macrocycles, greatly enhanced catalytic efficiency and excellent stereocontrol has been achieved, as triggered by anion-complexation induced acidity enhancement and enzyme-like pocket formation. Then I will present a substrate-induced assembly system that enables a dynamic cooperative activation network for efficient and enantioselective catalysis. The establishment of the enzyme-like induced-fit system was inspired from sulfate-induced macrocyclic dimerization assembly. Lastly, I will go across our efforts on fabricating chiral molecular cage catalysts possessing electron-deficient π surfaces. Through interplay of multiple anion-π interactions and base sites in a confined π-acidic cavity, we have established novel π-acid cooperative asymmetric catalysis.

Anion-recognition directed supramolecular catalysis

ACS Spring Meeting 2021

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