Organic letters

Synthesis of 3-arylpiperidines by a radical 1, 4-aryl migration

A Gheorghe, B Quiclet-Sire, X Vila, SZ Zard

Index: Gheorghe, Alexandra; Quiclet-Sire, Beatrice; Vila, Xavier; Zard, Samir Z. Organic Letters, 2005 , vol. 7, # 8 p. 1653 - 1656

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Citation Number: 36

Abstract

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.