Exploiting Iminoquinones as Electrophilic at Nitrogen “N+” Synthons for C–N Bond Construction

Exploiting Iminoquinones as Electrophilic at Nitrogen “N+” Synthons for C–N Bond Construction

New methods for C–N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under si...

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Bibliographic Details
Published in:Organic letters Vol. 23; no. 18; pp. 7008 - 7013
Main Authors: Mori-Quiroz, Luis M, Comadoll, Chelsea G, Super, Jonathan E, Clift, Michael D
Format: Journal Article
Language:English
Published: American Chemical Society 17-09-2021
Online Access:Get full text
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Summary:New methods for C–N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00867