Narrow-rim functionalization of calix[4]arenes via Sonogashira coupling reactions

被引：43

作者：

Al-Saraierh, H ^{[1
]}

Miller, DO ^{[1
]}

Georghiou, PE ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 21期

关键词：

D O I：

10.1021/jo050488s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.

引用

页码：8273 / 8280

页数：8

共 36 条

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