Moorthy, Suresh;
Castillo Bonillo, Alvaro;
Lambert, Hugues;
Kalenius, Elina;
Lee, Tung-Chun;
(2022)
Modulating the reaction pathway of phenyl diazonium ions using host-guest complexation with cucurbit[7]uril.
Chemical Communications
, 58
(22)
pp. 3617-3620.
10.1039/d1cc06982a.
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Abstract
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 α-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 ∼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.
| Type: | Article |
|---|---|
| Title: | Modulating the reaction pathway of phenyl diazonium ions using host-guest complexation with cucurbit[7]uril |
| Location: | England |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d1cc06982a |
| Publisher version: | https://doi.org/10.1039/D1CC06982A |
| Language: | English |
| Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/). |
| UCL classification: | UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > MAPS Faculty Office > Institute for Materials Discovery UCL > Provost and Vice Provost Offices > UCL BEAMS UCL UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > MAPS Faculty Office |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10144370 |
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