Selective Hydroboration-Oxidation of Terminal Alkenes under Flow Conditions

Chemistry. 2020 Sep 4;26(50):11423-11425. doi: 10.1002/chem.202001650. Epub 2020 Aug 6.

Abstract

An efficient flow process for the selective hydroboration and oxidation of different alkenes using 9-borabicyclo(3.3.1)nonane (9-BBN) allows facile conversion in high productivity (1.4 g h-1 ) of amorpha-4,11-diene to the corresponding alcohol, which is an advanced intermediate in the synthesis of the antimalarial drug artemisinin. The in situ reaction of borane and 1,5-cyclooctadiene using a simple flow generator proved to be a cost efficient solution for the generation of 9-BBN.

Keywords: alcohols; alkenes; flow chemistry; hydroboration; oxidation.