Benzannulation via Ruthenium-Catalyzed Diol–Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes

• Published in: Journal of the American Chemical Society Vol. 136; no. 16; pp. 5920 - 5922
• Main Authors: Geary, Laina M, Chen, Te-Yu, Montgomery, T. Patrick, Krische, Michael J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 23.04.2014; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Multidisciplinary; Cycloaddition Reaction; Fluorenes - chemical synthesis; Fluorenes - chemistry; Physical Sciences; polycyclic aromatic hydrocarbons; ruthenium; Ruthenium - chemistry; Science & Technology; standard operating procedures; DEOXYDEHYDRATION; LARGER ACENES; COMPLEXES; CHEMISTRY; HETEROACENES; HYDROXYCARBONYL; FISSION

A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol–diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol...