posted on 2002-07-23, 00:00authored byAlois Fürstner, Victor Mamane
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
π-coordination of the alkyne unit followed by interception
of the resulting η2-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.