Herein, an improved methodology for aryl-cubane cross-coupling is reported. The peculiarities of the cubane core and its behavior during cross-coupling conditions were analyzed, while the versatility of this adapted Baran cross-coupling methodology was demonstrated by the synthesis of various aryl-cubane systems, including coupling products of cubanes and porphyrins. Furthermore, arm extension of alkynyl-cubanes by Sonogashira reactions is demonstrated, showcasing the first proof of the stability of the cubane core in the presence of palladium catalysts.
Keywords: Sonogashira coupling; cross-coupling; cubanes; nickel catalysis; porphyrinoids.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.