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

被引:8
|
作者
Moorthy, Suresh [1 ]
Bonillo, Alvaro Castillo [1 ,2 ]
Lambert, Hugues [1 ,2 ]
Kalenius, Elina [3 ]
Lee, Tung-Chun [1 ,2 ]
机构
[1] Univ Coll London UCL, Inst Mat Discovery, London WC1H 0AJ, England
[2] Univ Coll London UCL, Dept Chem, London WC1H 0AJ, England
[3] Univ Jyvaskyla, Nanosci Ctr, Dept Chem, Jyvaskyla, Finland
基金
英国工程与自然科学研究理事会;
关键词
SUPRAMOLECULAR CATALYSIS; CUCURBITURIL; DEDIAZONIATION; ARENEDIAZONIUM; STABILIZATION;
D O I
10.1039/d1cc06982a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:3617 / 3620
页数:4
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