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Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions
Author(s) -
Elsherbini Mohamed,
Huynh Florence,
Dunbabin Alice,
Allemann Rudolf K.,
Wirth Thomas
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001650
Subject(s) - hydroboration , chemistry , nonane , borane , flow chemistry , organic chemistry , combinatorial chemistry , catalysis
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.