Synlett 2012; 23(19): 2763-2767
DOI: 10.1055/s-0032-1316556
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© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance

Yusuke Ano
a   Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: +81(6)68797396   eMail: chatani@chem.eng.osaka-u.ac.jp
,
Mamoru Tobisu*
b   Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: +81(6)68797396   eMail: tobisu@chem.eng.osaka-u.ac.jp
,
Naoto Chatani*
a   Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: +81(6)68797396   eMail: chatani@chem.eng.osaka-u.ac.jp
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Publikationsverlauf

Received: 18. April 2012

Accepted after revision: 28. Mai 2012

Publikationsdatum:
16. Juli 2012 (online)


Abstract

The ruthenium-catalyzed direct alkynylation of arenes with the chelation assistance of nitrogen-containing heterocycles including pyridine, pyrimidine, pyrazole, and imidazole are described. The alkynylation is successful even in the presence of an acidic N–H bond. Broad compatibility with functional groups is observed under catalytic conditions. The obtained alkynylated products could serve as precursors for polycyclic heteroarenes.

Supporting Information