Issue 13, 2011
From the journal:

Organic & Biomolecular Chemistry

Investigating N-methoxy-N′-aryl ureas in oxidative C–H olefination reactions: an unexpected oxidation behaviour†

Jens Willwacher,a   Souvik Rakshitb  and  Frank Glorius*a  

* Corresponding authors

a Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, Germany
E-mail: glorius@uni-muenster.de
Tel: +49 251 8333248

b Columbia University, Department of Chemistry, 3000 Broadway MC 3101, New York, USA

Abstract

Herein, we report a urea derived directing group for mild and highly selective oxidative C–H bond olefination. Subsequent intramolecular Michael addition affords dihydroquinazolinones in good yields. The N–O bond of the urea substrate exhibits superior oxidative behaviour compared to a variety of other external oxidants.

Graphical abstract: Investigating N-methoxy-N′-aryl ureas in oxidative C–H olefination reactions: an unexpected oxidation behaviour

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Article information

DOI
https://doi.org/10.1039/C1OB05636K
Article type
Communication
Submitted
21 Apr 2011
Accepted
11 May 2011
First published
12 May 2011

Org. Biomol. Chem., 2011,9, 4736-4740

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Investigating N-methoxy-N′-aryl ureas in oxidative C–H olefination reactions: an unexpected oxidation behaviour

J. Willwacher, S. Rakshit and F. Glorius, Org. Biomol. Chem., 2011, 9, 4736 DOI: 10.1039/C1OB05636K

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