Palladium catalyzed reaction of ortho-functionalized aryl iodides with bicyclic hydrazines: facile route toward heteroannulated cyclopentenes and azabicycles

A palladium catalyzed tandem protocol for the synthesis of cyclopentene fused heterocycles from diazabicyclic alkenes and ortho-functionalized aryl iodides has been elaborated. This tandem protocol was utilized for the synthesis of a number of cyclopentene fused dihydrobenzofurans and indolines. The reaction can be tuned toward the formation of either 3,4-disubstituted cyclopentenes or cyclopentene fused heterocycles by careful manipulation of the reaction parameters. The reaction was also extended to bicyclic alkenes derived from fulvene, which resulted in the heteroannulation of the azabicyclic system.