One-Step Annulative π-Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o-chloranil Catalysis
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- 作者：Dr. Kyohei Ozaki ; Keiichiro Murai ; Wataru Matsuoka ; Dr. Katsuaki Kawasumi ; Dr. Hideto Ito and Prof. Dr. Kenichiro Itami
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：January 24, 2017
- 年：2017
- 卷：56
- 期：5
- 页码：1361-1364
- 全文大小：1315K
- ISSN：1521-3773
文摘
Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one-step annulative π-extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o-chloranil catalyst system and dibenzosiloles or dibenzogermoles as π-extending agents, a variety of diarylacetylenes are transformed successfully into 9,10-diarylphenanthrenes in a single step with good functional-group tolerance. Furthermore, double π-extension reactions of 1,4-bis(phenylethynyl)benzene and diphenyl-1,3-butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes.