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J Am Chem Soc. 2011 May 4;133(17):6557-9. doi: 10.1021/ja201931e. Epub 2011 Apr 7.

Phenanthrene synthesis by iron-catalyzed [4+2] benzannulation between alkyne and biaryl or 2-alkenylphenyl Grignard reagent.

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  • 1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.


The [4+2] benzannulation reaction of internal or terminal alkynes with 2-biaryl, 2-heteroarylphenyl, or 2-alkenylphenyl Grignard reagents in the presence of Fe(acac)(3), 4,4'-di-tert-butyl-2,2'-bipyridyl, and 1,2-dichloro-2-methylpropane takes place at room temperature in 1 h to give 9-substituted or 9,10-disubstituted phenanthrenes and congeners in moderate to excellent yields. The reaction tolerates sensitive functional groups such as bromide and olefin. When applied to a 1,3-diyne, the annulation reaction takes place on both acetylenic moieties to give a bisphenanthrene derivative.

© 2011 American Chemical Society

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