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Flow dearomatization of electron-poor 3-fluoromethylthioindoles by 1,3-dipolar cycloaddition

Flow dearomatization of electron-poor 3-fluoromethylthioindoles by 1,3-dipolar cycloaddition Indoles substituted by electron-depleted thio groups at positions 1 and 3 react as C2 = C3 dipolarophiles with an electron-rich azomethine ylide dipole under flow conditions. The dearomatizing (3 + 2) cycloadditions readily occur to afford the corresponding fluorinated 3D-pyrrolidinoindolines bearing a tetrasusbtituted carbon centre at the ring junction. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Flow dearomatization of electron-poor 3-fluoromethylthioindoles by 1,3-dipolar cycloaddition

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2021
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-021-00203-z
Publisher site
See Article on Publisher Site

Abstract

Indoles substituted by electron-depleted thio groups at positions 1 and 3 react as C2 = C3 dipolarophiles with an electron-rich azomethine ylide dipole under flow conditions. The dearomatizing (3 + 2) cycloadditions readily occur to afford the corresponding fluorinated 3D-pyrrolidinoindolines bearing a tetrasusbtituted carbon centre at the ring junction.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jun 1, 2022

Keywords: Organofluorine chemistry; Dearomatization; (3 + 2)-Cycloaddition; Electron-poor arenes; Hetero-aromatics

References