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PBr 介导的 1,7-二炔-3,6-双(丙炔碳酸酯)环化反应:5-溴代四环的合成。

PBr-Mediated Cyclization of 1,7-Diyn-3,6-bis(propargyl carbonate)s: Synthesis of 5-Bromotetracenes.

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, People's Republic of China.

出版信息

J Org Chem. 2017 Oct 6;82(19):10051-10061. doi: 10.1021/acs.joc.7b01519. Epub 2017 Sep 11.

DOI:10.1021/acs.joc.7b01519
PMID:28845663
Abstract

A new and straightforward method for the synthesis of 5-bromotetracenes through PBr-mediated cyclization of 1,7-diyn-3,6-bis(propargyl carbonate)s has been developed. This method offers several advantages such as easily accessible starting materials, high efficiency, and wide functional group compatibility. In addition, chloro- and iodo-substituted tetracenes were also synthesized using appropriate halogenating reagents. The utility of the 5-bromotetracene products has been illustrated by their efficient transformations through various palladium-catalyzed cross-coupling reactions.

摘要

一种通过 PBr3 介导的 1,7-二炔-3,6-双(丙炔碳酸酯)环化反应合成 5-溴并四苯的新的、简单的方法已经被开发出来。该方法具有原料易得、效率高、官能团兼容性广等优点。此外,还使用适当的卤化试剂合成了氯代和碘代并四苯。通过各种钯催化交叉偶联反应,5-溴并四苯产物的实用性得到了很好的证明。

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