Regioselective Reductive Heck Arylation of a Rigid Tetracyclic Oxanorbornene Scaffold

Reductive Heck arylation of the tetracyclic oxanorbornene (1) was found to proceed with complete regioselectivity. A number of aryl iodides were investigated, all giving the same selectivity. Modifications within the scaffold were also tested, giving a 84:16 ratio of regioisomers in the worst case. The regioselectivity is probably due to steric factors.