Synlett 2016; 27(11): 1707-1710
DOI: 10.1055/s-0035-1561940
letter
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives

Tomoya Nagata
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   eMail: miura@chem.eng.osaka-u.ac.jp
,
Tetsuya Satoh*
b   Department of Chemistry, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan   eMail: satoh@sci.osaka-cu.ac.jp
,
Yuji Nishii
c   Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Masahiro Miura*
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   eMail: miura@chem.eng.osaka-u.ac.jp
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Publikationsverlauf

Received: 29. Januar 2016

Accepted after revision: 28. Februar 2016

Publikationsdatum:
24. März 2016 (online)


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Abstract

A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuterium-labeling experiments indicated the involvement of five-membered rhodacycle intermediates.

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