A novel reductive tetraallylation of pyridine

Pyridine and 4-picoline undergo reductive tetraallylation with allyl bromide and zinc dust in THF at room temperature to afford regio-selectively 1,2,3,6-tetraallyl-1,2,3,6-tetrahydropyridine and 1,2,3,6-tetraallyl-1,2,3,6-tetrahydro-4-picoline, respectively.