具有空前位阻能力的环芳烷在芳基碘𬭩盐氟代反应中的应用。
Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts.
机构信息
Department of Chemistry and Nebraska Center for Materials and Nanoscience, University of Nebraska, Lincoln, Nebraska 68588-0304, USA.
出版信息
Org Lett. 2011 Jun 17;13(12):3158-61. doi: 10.1021/ol201080c. Epub 2011 May 17.
Abstract
For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.
摘要
首次表明，在二芳基碘氟化物的还原消除反应中，特别富电子的芳环可以仅被氟化。5-甲氧基[2.2]对环芳烷-4-基导向基团通过空间和电子效应的结合，同时减少了无效的芳炔化学和消除配体交换反应。环芳烷导向基团的使用允许在二芳基碘氟化物的氟化反应中实现前所未有的控制程度。
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