Synthesis of Regioselectively Functionalized Pyrenes via Transition-Metal-Catalyzed Electrocyclization

graphical abstract

D. B. Walker, J. Howgego, A. P. Davis*

Synthesis-Stuttgart, 2010, 21, 3686-3692


Transition-metal-catalyzed electrocyclic rearrangement of 2,6-diethynyl-1,1′-biphenyl precursors to form polysubstituted pyrenes is described. This method is useful for the preparation of pyrenes with uncommon substitution patterns, and selective integration of functional groups at the 1-, 2-, 3-, 5-, 7- and 9-positions is demonstrated.