Synlett, Table of Contents Synlett 2013; 24(17): 2297-2301DOI: 10.1055/s-0033-1339710 letter © Georg Thieme Verlag Stuttgart · New YorkSynthesis of Phenanthrenes by Cationic Chromium(III) Porphyrin-Catalyzed Dehydration Cycloaromatization Ryota Wakabayashi a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan Fax: +81(75)3832438 Email: kurahashi.takuya.2c@kyoto-u.ac.jp Email: matsubara.seijiro.2e@kyoto-u.ac.jp , Takuya Kurahashi* a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan Fax: +81(75)3832438 Email: kurahashi.takuya.2c@kyoto-u.ac.jp Email: matsubara.seijiro.2e@kyoto-u.ac.jp b JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan , Seijiro Matsubara* b JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract Readily available biphenyl derivatives with ortho oxirane moiety react in the presence of cationic chromiun(III) porphyrin catalyst to afford phenanthrenes. The reaction is considered to be triggered by activation of the oxirane moiety through coordination to the Lewis acidic cationic chromium to give aldehyde via 1,2-hydride shift, which reacts with arene through intramolecular electrophilic aromatic substitution and subsequent dehydration. The reaction allows constructing a variety of polycyclic aromatic and heteroaromatic compounds. Key words Key wordsarene - chromium - cyclization - porphyrin - transition metals Full Text References References and Notes For some selected examples, see: 1a Chen Y.-H, Chou H.-H, Su T.-H, Chou P.-Y, Wu F.-I, Cheng C.-H. Chem. Commun. 2011; 47: 8865 1b Mitsuhashi R, Suzuki Y, Yamanari Y, Mitamura H, Kambe T, Ikeda N, Okamoto H, Fujiwara A, Yamaji M, Kawasaki N, Maniwa Y, Kubozono Y. Nature (London) 2010; 464: 76 1c Song S, Jin Y, Kim K, Kim SH, Shim YB, Lee K, Suh H. Tetrahedron Lett. 2008; 49: 3582 1d He B, Tian H, Geng Y, Wang F, Müllen K. Org. Lett. 2008; 10: 773 1e Kim H.-J, Lee E, Park H.-S, Lee M. 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