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

Autor:	Suresh Moorthy, Alvaro Castillo Bonillo, Hugues Lambert, Elina Kalenius, Tung-Chun Lee
Rok vydání:	2022
Předmět:	Bridged-Ring Compounds Ions Imidazoles supramolekulaarinen kemia Materials Chemistry Metals and Alloys Ceramics and Composites Water General Chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials
Zdroj:	Chemical Communications. 58:3617-3620
ISSN:	1364-548X 1359-7345
DOI:	10.1039/d1cc06982a
Popis:	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. peerReviewed
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::db2212a2c23618ec6e08302956cb8c51 https://doi.org/10.1039/d1cc06982a Zobrazit plný text záznamu