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Short Paper | Regular issue | Vol 91, No. 8, 2015, pp.1654-1659
Published online, 10th July, 2015
DOI: 10.3987/COM-15-13255
■ Development of an Efficient Process for 3,6-Dihydro-2H-pyran-4-boronic Acid Pinacol Ester

Feng Xue,* Yong Zhu, and Chang-Gong Li

*Key Laboratory of Functional Organic Molecules of Xinxiang City Henan Province, College of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang Henan, 453002, China

Abstract

An efficient process for the synthesis of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester has been developed in one-pot manner. Starting from the condensation of 4-tetrahydropyranone with hydrazine hydrate, the subsequent treatment of hydrazone with copper(II) bromide-triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) conveniently gave 4-bromo-3,6-dihydro-2H-pyran, which was then conducted through palladium-catalyzed borylation to afford the desired product using a low loading of a Pd catalyst.