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

Authors
Klumpp, DA Beauchamp, PS Sanchez, GV Aguirre, S de Leon, S
Citation
Da. Klumpp et al., Superacid-catalyzed preparation of aryl-substituted piperidines via dicationic electrophiles, TETRAHEDR L, 42(34), 2001, pp. 5821-5823
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
34
Year of publication
2001
Pages
5821 - 5823
Database
ISI
SICI code
0040-4039(20010820)42:34<5821:SPOAPV>2.0.ZU;2-Y
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-tetrahydrop yridines react with arenes to give aryl-substituted piperidines. It is prop osed that the reactions occur through dicationic electrophilic intermediate s. Depending upon substituents, either 1,4-dications or 1,3-dications are f ormed. The dicationic intermediates react with moderately deactivated arene s, such as o-dichlorobenzene. (C) 2001 Elsevier Science Ltd. All rights res erved.