Allybboranes: reductive mono- and trans-diallylation of aromatic nitrogen heterocycloc compounds

Reductive α-monoallylation of pyrrole, indole, quinolines, isoquinolines and phenathridine as well as reductive trans-α, α'-diallylation of pyridines, 4.4'-dipyridil, pyrrole and isoquinoline by allylic boranes were discovered. A convenient method for trans- to cis-isomerization of trans-2,5-diallylpyrrolidine and trans-2,6-diallyl-1,2,5,6-tetrahydropyridines was also found. The discovered reactions unite heterocyclic and organoboron chemistries on a novel level. 50 refs., 2 tabs