Journal
SCIENCE CHINA-CHEMISTRY
Volume 62, Issue 6, Pages 713-718Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-018-9427-4
Keywords
coordination-assembly; cage; encapsulation; Knoevenagel condensation
Categories
Funding
- National Natural Science Foundation of China [21825107, 21601183, 21801241, 21571090]
- Natural Science Foundation of Fujian Province [2016J05051, 2017J05037]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
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A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages' cavity is crucial for their applications in supramolecular catalysis.
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