Brandhofer, Tobias and Gini, Andrea and Stockerl, Sebastian and Piekarski, Dariusz G. and Mancheno, Olga Garcia (2019) Direct C-H Bond Imidation with Benzoyl Peroxide as a Mild Oxidant and a Reagent. JOURNAL OF ORGANIC CHEMISTRY, 84 (20). pp. 12992-13002. ISSN 0022-3263, 1520-6904
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A simple and mild Cu-catalyzed oxidative three component oxidative Ugi-type method for the synthesis of a variety of substituted imides has been developed. In this direct imidation approach, benzoyl peroxide serves as both the oxidant and the carboxylate source, allowing not only the functionalization of C(sp(3))-H bonds in alpha-position to an amine but also benzylic substrates. This procedure presents a wide substrate-type and functional group tolerance. Moreover, the mildness of the method permitted us to extend its application to the late stage functionalization of complex natural products such as the alkaloids brucine and strychnine, leading to interesting highly functionalized imide derivatives. On the basis of experimental and computational studies, a plausible mechanism has been proposed.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DIRECT FUNCTIONALIZATION; COUPLING REACTION; RING EXPANSION; BASIS-SETS; IMIDES; OXIDATION; AMIDES; AMINES; APPROXIMATION; LENALIDOMIDE; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 Mar 2020 09:06 |
| Last Modified: | 25 Mar 2020 09:06 |
| URI: | https://pred.uni-regensburg.de/id/eprint/25988 |
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