Exploiting Iminoquinones as Electrophilic at Nitrogen “N+” Synthons for C–N Bond Construction
- 3 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7008-7013
- https://doi.org/10.1021/acs.orglett.1c00867
Abstract
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.Keywords
Funding Information
- University of Kansas
- National Institute of General Medical Sciences (GM113117)
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