Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 17, Pages 6557-6559Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja201931e
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Funding
- MEXT from the Japan Science and Technology Agency, JST [22000008]
- Global COE Program for Chemistry Innovation
- Japan Society for the Promotion of Science [21.8684]
- Grants-in-Aid for Scientific Research [22000008, 23750100] Funding Source: KAKEN
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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 I 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.
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