Reductive heck reactions and [3+2] cycloadditions of unsaturated N,N'-bistricyclic imides

Abstract

The C-C coupling of N,N'-bis(5-norbornene-2,3-dicarboximide) (3) and N,N'-bis(7-oxa-5-norbornene-2,3-dicarboximide) (6) with aryl and heteroaryl iodides gave under reductive Heck conditions the C-aryl(hetaryl), substituted N,N'-bistricyclic imides 7a-f and 8a,b. The fused spiro-1,3- indandionolylpyrrolidine compounds, 9, 10 and 11 were also obtained from ninhydrine, sarcosine and 3 or 6 via [3+2]cycloaddition.