Appending aromatic moieties at thepara-
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- 作者：Francesco Troisi ; Teresa Pierro ; Carmine Gaeta ; Michele Carratù ; Placido Neri
- 关键词：Calixarene exo-rim ; p-Bromodienone route ; Inherently chiral calixarenes ; Dienone– ; phenol rearrangement ; Meta-substituted calixarenes
- 刊名：Tetrahedron Letters
- 出版年：2009
- 出版时间：5 August 2009
- 年：2009
- 卷：50
- 期：31
- 页码：4416-4419
- 全文大小：1541 K
文摘
The silver-mediated nucleophilic substitution on calixarene p-bromodienone derivatives (the ‘p-bromodienone route’) with activated aromatic substrates allows the introduction of aromatic moieties at the para- or meta-position of calixarene aromatic rings. Less reactive substrates mainly afford C–O para-coupled derivatives, while more activated ones mainly give inherently chiral, C–C meta-coupled products through a dienone–phenol rearrangement of the intermediate dienone derivative. Examples of C–C para-coupling and O–C coupling at the endo calixarene oxygen atom were also observed.