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

Alessandro   B.C.   Simas; Daniel   L.   de Sales; Samir   F.A.   Cavalcante; Cristina   M.   de Medeiros; Sandro   H.S.   Moraes; Erika   M.   de Carvalho

doi:10.2174/157017808785982149

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

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Letters in Organic Chemistry

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

Volume: 5 Issue: 7

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

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

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.

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Simas B.C. Alessandro, de Sales L. Daniel, Cavalcante F.A. Samir, de Medeiros M. Cristina, Moraes H.S. Sandro and de Carvalho M. Erika, Palladium-Catalyzed Cross-Couplings of 2-Tributylstannyl-N-Boc-2,3- Dehydropiperidine, a Cyclic Enecarbamate, Letters in Organic Chemistry 2008; 5 (7) . https://dx.doi.org/10.2174/157017808785982149