Regioselective synthesis of 1,2-dihydropyridines by rhodium-catalyzed hydroboration of pyridines.

J Am Chem Soc

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

Published: February 2012

Pyridine undergoes addition of pinacolborane at 50 °C in the presence of a rhodium catalyst, giving N-boryl-1,2-dihydropyridine in a high yield. The selective 1,2-hydroboration also takes place in the reactions of substituted pyridines. In the reaction of 3-substituted pyridines, 3-substituted N-boryl-1,2-dihydropyridines are formed regioselectively.

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http://dx.doi.org/10.1021/ja3002953DOI Listing

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