ORGANIC SYNTHESIS

Closing rings with porous templates

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Science  14 Feb 2020:
Vol. 367, Issue 6479, pp. 753-754
DOI: 10.1126/science.367.6479.753-f

The closure of large rings from linear substrates (macrocyclization) must avoid the competing coupling between molecules and the entropic penalty for folding long chains. Hydrophobic nanoscale cavities can assist in both folding of chains and avoiding intermolecular reactions. Liu et al. used a self-assembling molecule bearing bent chains of aromatic groups to create two-dimensional sheets with ∼2-nanometer pores. A palladium(0) catalyst performed Suzuki couplings on linear substrates bound in the pores to create >30-mer macrocycles. On formation, the macrocycles released spontaneously to enable subsequent rounds of reaction.

J. Am. Chem. Soc. 142, 1904 (2020).

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