Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions

Mohamed Elsherbini; Florence Huynh; Alice Dunbabin; Rudolf K. Allemann; Thomas Wirth

doi:10.1002/chem.202001650

Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions

Mohamed Elsherbini, Florence Huynh, Alice Dunbabin, Rudolf K. Allemann, Thomas Wirth

Cardiff University

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	11423-11425
Number of pages	3
Journal	Chemistry - A European Journal
Volume	26
Issue number	50
Early online date	24 Apr 2020
DOIs	https://doi.org/10.1002/chem.202001650
Publication status	Published - 4 Sept 2020
Externally published	Yes

Access to Document

10.1002/chem.202001650Licence: CC BY

Cite this

@article{25a8abd04561401b9e157cdbdd040fb4,

title = "Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions",

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",

author = "Mohamed Elsherbini and Florence Huynh and Alice Dunbabin and Allemann, \{Rudolf K.\} and Thomas Wirth",

year = "2020",

month = sep,

day = "4",

doi = "10.1002/chem.202001650",

language = "English",

volume = "26",

pages = "11423--11425",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "50",

}

TY - JOUR

T1 - Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions

AU - Elsherbini, Mohamed

AU - Huynh, Florence

AU - Dunbabin, Alice

AU - Allemann, Rudolf K.

AU - Wirth, Thomas

PY - 2020/9/4

Y1 - 2020/9/4

N2 - 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.

AB - 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.

KW - alcohols

KW - alkenes

KW - flow chemistry

KW - hydroboration

KW - oxidation

UR - https://www.scopus.com/pages/publications/85088986650

U2 - 10.1002/chem.202001650

DO - 10.1002/chem.202001650

M3 - Article

AN - SCOPUS:85088986650

SN - 0947-6539

VL - 26

SP - 11423

EP - 11425

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 50

ER -

Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions

Abstract

Access to Document

Other files and links

Fingerprint

Cite this