Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition??Metal Catalyzed Cycloisomerization Reactions

V Mamane, P Hannen, A Fürstner

Index: Mamane, Victor; Hannen, Peter; Fuerstner, Alois Chemistry - A European Journal, 2004 , vol. 10, # 18 p. 4556 - 4575

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Citation Number: 407

Abstract

Abstract Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl 2, AuCl, AuCl 3, GaCl 3 or InCl 3 in toluene. This 6-endo-dig cyclization likely proceeds through initial π-complexation of the alkyne unit followed by interception of the resulting η 2-metal species by the adjacent arene ring. The reaction is ...