Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 47, Pages 9405-9409Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26635k
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Funding
- National Natural Science Foundation of China [21272093]
- State Key Lab of Supramolecular Structure and Materials at Jilin University
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A practical and effective trifluoromethanesulfonic acid (TfOH)-catalyzed cyclooligomerization strategy was developed for the synthesis of functionalized pillar[n]arenes and copillar[5]arenes from 1,4-dialkoxybenzenes with paraformaldehyde under mild reaction conditions, and the reaction mechanism of solution-phase catalytic synthesis of pillararenes was investigated by room-temperature X-band ESR spectroscopy, mass spectroscopy, NMR and control experiments, suggesting a free radical process initially and a Friedel-Crafts alkylation process during the consequent coupling and ring-closure stage.
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