Flexible synthesis of phenanthrenes by PtCl2-catalyzed cycloisomerization 
reaction

Fürstner, A.; Mamane, V.

doi:10.1021/jo025962y

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Flexible synthesis of phenanthrenes by PtCl₂-catalyzed cycloisomerization reaction

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Fürstner, A.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mamane, V.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Mamane, V. (2002). Flexible synthesis of phenanthrenes by PtCl₂-catalyzed cycloisomerization reaction. Journal of Organic Chemistry, 67(17), 6264-6267. doi:10.1021/jo025962y.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-99A6-5

Abstract

Readily available biphenyl derivatives containing an alkyne unit at one of their ortho positions are converted into substituted phenanthrenes upon exposure to catalytic amounts of either PtCl2, AuCl3, GaCl3, or InCl3 in toluene. This 6-endo- dig cyclization likely proceeds through initial a-coordination of the alkyne unit followed by interception of the resulting eta(2)-metal complex by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product except C-9. Moreover, the reaction is readily applied to the heterocyclic series as exemplified by the preparation of benzoindoles, naphthothiophenes as well as bridgehead nitrogen heterocycles.