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

Full Text: HTML

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 ...

Related Articles:

Synthesis of [5]-,[6]-, and [7] helicene via Ni (0)-or Co (I)-catalyzed isomerization of aromatic cis, cis-dienetriynes

[Teply, Filip; Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Saman, David; Rulisek, Lubomir; Fiedler, Pavel Journal of the American Chemical Society, 2002 , vol. 124, # 31 p. 9175 - 9180]

Transition metal catalysed synthesis of tetrahydro derivatives of [5]-,[6]-and [7] helicene

[Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Teply, Filip; Vyskocil, Stepan; Saman, David Tetrahedron Letters, 1999 , vol. 40, # 10 p. 1993 - 1996]

Syntheses of [5]-helicene by McMurry or carbenoid couplings

[Dubois, Fabien; Gingras, Marc Tetrahedron Letters, 1998 , vol. 39, # 28 p. 5039 - 5040]

Toward a visible light mediated photocyclization: Cu-based sensitizers for the synthesis of [5] helicene

[Hernandez-Perez, Augusto C.; Vlassova, Anna; Collins, Shawn K. Organic Letters, 2012 , vol. 14, # 12 p. 2988 - 2991]

Syntheses of [5]-helicene by McMurry or carbenoid couplings

[Dubois, Fabien; Gingras, Marc Tetrahedron Letters, 1998 , vol. 39, # 28 p. 5039 - 5040]

More Articles...