Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 34, Pages 5912-5915Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900982
Keywords
C-C coupling; Copper; Decarboxylation; Synthetic methods
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A mild and efficient strategy for decarboxylative C(sp(2))-C(sp(3)) and C(sp)-C(sp(3)) coupling of alpha,beta-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.
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