Palladium-catalyzed regioselective silaboration of pyridines leading to the synthesis of silylated dihydropyridines

Kazuyuki Oshima; Toshimichi Ohmura; Michinori Suginome

doi:10.1021/ja2020229

Palladium-catalyzed regioselective silaboration of pyridines leading to the synthesis of silylated dihydropyridines

J Am Chem Soc. 2011 May 18;133(19):7324-7. doi: 10.1021/ja2020229. Epub 2011 Apr 21.

Authors

Kazuyuki Oshima¹, Toshimichi Ohmura, Michinori Suginome

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

PMID: 21510608
DOI: 10.1021/ja2020229

Abstract

The addition of silylboronic esters to pyridine takes place in toluene at 50 °C in the presence of a palladium catalyst to give N-boryl-4-silyl-1,4-dihydropyridines in high yield. The regioselective 1,4-silaboration also proceeds in the reaction of 2-picoline and 3-substituted pyridines, whereas 4-substituted pyridines undergo 1,2-silaboration to give N-boryl-2-silyl-1,2-dihydropyridines regioselectively.