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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Narrow-rim functionalization of calix[4]arenes via Sonogashira coupling reactions.

The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.[1]

References

  1. Narrow-rim functionalization of calix[4]arenes via Sonogashira coupling reactions. Al-Saraierh, H., Miller, D.O., Georghiou, P.E. J. Org. Chem. (2005) [Pubmed]
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