Issue 34, 2011
From the journal:

Chemical Communications

Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis†

Eiji Shirakawa,*a   Seiji Masui,a   Rintaro Narui,a   Ryo Watabe,a   Daiji Ikedaa  and  Tamio Hayashi*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto, Japan
E-mail: shirakawa@kuchem.kyoto-u.ac.jp

Abstract

Phenyl- and vinyllithiums having an alkyl substituent at their ortho- and cis-position, respectively, readily added to alkynes in the presence of 5 mol% of Fe(acac)3. The reaction of o-(trimethylsilyl)phenyllithium with alkynes gave benzosiloles through an addition–cyclization sequence.

Graphical abstract: Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis

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Article information

DOI
https://doi.org/10.1039/C1CC11989C
Article type
Communication
Submitted
08 Apr 2011
Accepted
11 Jul 2011
First published
25 Jul 2011

Chem. Commun., 2011,47, 9714-9716

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Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis

E. Shirakawa, S. Masui, R. Narui, R. Watabe, D. Ikeda and T. Hayashi, Chem. Commun., 2011, 47, 9714 DOI: 10.1039/C1CC11989C

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