Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions. Issue 50 (6th August 2020)

• Record Type: Journal Article
• Authors: Elsherbini, Mohamed; Huynh, Florence; Dunbabin, Alice; Allemann, Rudolf K.; Wirth, Thomas
• Is Part Of: Chemistry. Volume 26:Issue 50(2020)
• Page Start: 11423
• Page End: 11425
• Publication Date: 2020-08-06
• Subjects: alcohols -- alkenes -- flow chemistry -- hydroboration -- oxidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001650
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : An efficient and scalable flow protocol for the selective hydroboration–oxidation of terminal alkenes enabled easy access to dihydroartemisinic alcohol, an advanced intermediate in the synthesis of the antimalarial drug artemisinin.