Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration.
[reaction: see text] A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.
Gheorghe
Alexandru
A
Laboratoire de Synthèse Organique, Département de Chimie, Ecole Polytechnique, Route de Saclay, 91128 Palaiseau Cedex, France.
Quiclet-Sire
Béatrice
B
Vila
Xavier
X
Zard
Samir Z
SZ