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One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/ o ‐chloranil Catalysis
Author(s) -
Ozaki Kyohei,
Murai Keiichiro,
Matsuoka Wataru,
Kawasumi Katsuaki,
Ito Hideto,
Itami Kenichiro
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201610374
Subject(s) - palladium , chloranil , catalysis , chemistry , cationic polymerization , benzene , functional group , combinatorial chemistry , organic chemistry , polymer
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.