One-Step Annulative [pi]-Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o-chloranil Catalysis

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 pre...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 5; p. 1361
Main Authors Ozaki, Kyohei, Murai, Keiichiro, Matsuoka, Wataru, Kawasumi, Katsuaki, Ito, Hideto, Itami, Kenichiro
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 24.01.2017
EditionInternational ed. in English
Subjects
Alkynes
Benzene
Catalysis
Chloranil
Materials science
Palladium
Polycyclic aromatic hydrocarbons
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201610374