Letters in Organic Chemistry

Author(s): Alessandro B.C. Simas, Daniel L. de Sales, Samir F.A. Cavalcante, Cristina M. de Medeiros, Sandro H.S. Moraes and Erika M. de Carvalho

DOI: 10.2174/157017808785982149

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Palladium-Catalyzed Cross-Couplings of 2-Tributylstannyl-N-Boc-2,3- Dehydropiperidine, a Cyclic Enecarbamate

Page: [587 - 590] Pages: 4

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Abstract

Cross-couplings of 2-tributylstannyl-N-Boc-2,3-dehydropiperidine, a six-membered cyclic enecarbamate, with aryl iodides and triflates are reported for the first time. Under the Pd(0)/AsPh3 catalytic system (Farinas conditions), better conversions of this challenging substrate into the expected products were achieved with shorter reactions carried out under higher temperature.

Keywords: Stille coupling, piperidine, synthesis, heterocycle, cyclic amine, Umpolung