Direct assembly of polyarenes via C-C coupling Using PIFA/BF3·Et2O.
Direct oxidative Kita-type coupling between naphthalene and substituted benzenes was found to proceed via four-component coupling, leading to a linear tetraarene with a binaphthalene core. The methodology was extendable to the coupling of unfunctionalized 1,1'-binaphthalene with mesitylene to give a linear hexaarene product in a remarkably chemoselective manner in 87% yield. The method represents an attractive alternative to the traditional syntheses of related oligonaphthalene products via a sequence of metal-catalyzed cross-coupling steps.
Department of Chemistry, Universitat Autònoma de Barcelona, 08193-Cerdanyola del Vallès, Barcelona, Spain.
Enrico
E
Faggi
Rosa M
RM
Sebastián
Roser
R
Pleixats
Adelina
A
Vallribera
Alexandr
A
Shafir
Alejandra
A
Rodríguez-Gimeno
Carmen
C
Ramírez de Arellano