4.7 Article

Modulating the reaction pathway of phenyl diazonium ions using host-guest complexation with cucurbit[7]uril

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 22, Pages 3617-3620

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc06982a

Keywords

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Funding

  1. Leverhulme Trust [RPG-2016393]
  2. EPSRC [EP/P020194/1]
  3. EPSRC M3S CDT [EP/L015862/1]

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A new supramolecular approach has been reported to selectively deactivate the electrophilic alpha-carbon of phenyl diazonium ion through host-guest complexation, thus avoiding undesirable side reactions. This method holds great potential for the reactive chemistry of organic molecules in aqueous media.
Aryl diazonium ions are known to be an important intermediate in the divergent synthesis of azo compounds and substituted aromatics. The presence of more than one electrophilic center in a diazonium ion could lead to undesirable side reactions during a synthesis. Herein, we report that the electrophilic alpha-carbon on a phenyl diazonium [PhN2](+) ion can be selectively deactivated upon host-guest complexation with cucurbit[7]uril (CB7) in aqueous media, achieving a similar to 60-fold increase in the half-life of [PhN2](+). Notably, however, the electrophilic nitrogen of the encapsulated diazonium ion remains active towards diazo coupling with strong nucleophiles, allowing the formation of azo compounds using a two-month-old aqueous solution of [CB7-PhN2](+). Our supramolecular approach can open new possibilities for the reactive chemistry of organic molecules in aqueous media.

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