Superacid-catalyzed preparation of aryl-substituted piperidines via dicationic electrophiles

…, PS Beauchamp, GV Sanchez, S Aguirre, S de Leon

Index: Klumpp, Douglas A.; Beauchamp, Philip S.; Sanchez Jr., Gregorio V.; Aguirre, Sharon; De Leon, Sarah Tetrahedron Letters, 2001 , vol. 42, # 34 p. 5821 - 5823

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Citation Number: 20

Abstract

The electrophilic chemistry of 1, 2, 3, 6-tetrahydropyridines has been studied in the Bronsted superacid, CF3SO3H (triflic acid). The 1, 2, 3, 6-tetrahydropyridines react with arenes to give aryl-substituted piperidines. It is proposed that the reactions occur through dicationic electrophilic intermediates. Depending upon substituents, either 1, 4-dications or 1, 3- dications are formed. The dicationic intermediates react with moderately deactivated ...